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Tetrahedron Letters
Journal Prestige (SJR): 0.683
Citation Impact (citeScore): 2
Number of Followers: 121  
 
  Hybrid Journal Hybrid journal (It can contain Open Access articles)
ISSN (Print) 0040-4039 - ISSN (Online) 1359-8562
Published by Elsevier Homepage  [3162 journals]
  • Graphical abstract TOC
    • Abstract: Publication date: 12 December 2018Source: Tetrahedron Letters, Volume 59, Issue 50Author(s):
       
  • Graphical abstract TOC
    • Abstract: Publication date: 12 December 2018Source: Tetrahedron Letters, Volume 59, Issue 50Author(s):
       
  • Graphical abstract TOC cont’d
    • Abstract: Publication date: 12 December 2018Source: Tetrahedron Letters, Volume 59, Issue 50Author(s):
       
  • Visible-light-induced 1,2-alkylarylation of alkenes with a-C(sp3)–H
           bonds of acetonitriles involving neophyl rearrangement under
           transition-metal-free conditions
    • Abstract: Publication date: Available online 17 November 2018Source: Tetrahedron LettersAuthor(s): Qiao-Lin Wang, Zan Chen, Cong-Shan Zhou, Bi-Quan Xiong, Pan-Liang Zhang, Chang-An Yang, Yu Liu, Quan Zhou An efficient visible-light-induced difunctionalization of alkenes with a-C(sp3)–H bonds of nitriles is described for the constructing of diverse 5-oxo-pentanenitriles under transition-metal-free conditions. This protocol proceeds via the functionalization of C(sp3)−H bond and radical addition/intramolecular 1,2-aryl migration processes, which features a wide scope of substituted α,α-diaryl allylic alcohols. The results of kinetic isotope experiments show that the cleavage of C(sp3)–H bond of acetonitriles is a rate-limiting step.Graphical abstractGraphical abstract for this article
       
  • Antiviral drug nevirapine as a template for hydrated imidazoline ring
           expansion (HIRE): rapid access to the diarene-fused 1,4,7-triazecine ring
           system
    • Abstract: Publication date: Available online 17 November 2018Source: Tetrahedron LettersAuthor(s): Sergey Grintsevich, Alexander Sapegin, Elena Reutskaya, Mikhail Krasavin The tricyclic ring system of the antiviral drug nevirapine has been employed to test the workability of the hydrated imidazoline ring expansion (HIRE) reaction which was previously exemplified for [1.4]oxazepine and [1.4]thiazepine counterparts. The imidazoline nucleus was grafted onto the lactam moiety of nevirapine in two high-yielding steps. Subsequent N-alkylation and the HIRE reaction proceeded as envisioned and delivered rare ring-expanded diarene-fused 1,4,7-triazecines with a diversity of alkyl substituents at the lactam nitrogen atom. These findings extend the scope of the HIRE reaction to the medicinally prominent [1.4]diazepine chemical space.Graphical abstractGraphical abstract for this article
       
  • Silver-Promoted Cross-Coupling of Substituted Allyl(trimethyl)silanes with
           Aryl Iodides by Palladium Catalysis
    • Abstract: Publication date: Available online 17 November 2018Source: Tetrahedron LettersAuthor(s): Zhen-Lin Hou, Fan Yang, Zhibing Zhou, Yu-Fei Ao, Bo Yao A ligand-free Pd-catalyzed cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides enabled by silver salts was developed. This reaction delivered allylic arenes chemoselectively and regioselectively. The study suggested that the reaction might proceed through oxidative addition of ArI to Pd(0) followed by halide abstraction to give an electrophilic complex ArPdX, which further reacted with allyl(trimethyl)silanes via electrophilic addition/desilylation/reductive elimination to afford the allyl-aryl coupling products.Graphical abstractGraphical abstract for this article
       
  • An approach towards the oxidation of 2-amino-4H-chromenes to
           2-imino-2H-chromenes
    • Abstract: Publication date: Available online 17 November 2018Source: Tetrahedron LettersAuthor(s): Manohar Mantipally, Rambabu Gundla, Madhusudhana Reddy Gangireddy, Viswanathan Vijayan, Velmurugan Devadasan A novel method for the synthesis of 2-imino-2H-benzo[h]chromenes via the sequential addition of N-chlorosuccinimide and triethylamine to 2-amino-4H-benzo[h]chromenes has been established. This reaction protocol represents an efficient synthetic strategy to form iminochromene derivatives under mild reaction conditions, which utilizes readily accessible aminochromenes as starting materials and tolerates a wide range of substrates.Graphical abstractGraphical abstract for this article
       
  • d-arabino-2-heptulosonates+(DAH)+from+shikimic+acid+based+on+silyl+group+migration&rft.title=Tetrahedron+Letters&rft.issn=0040-4039&rft.date=&rft.volume=">A short synthesis of protected 3-deoxy-d-arabino-2-heptulosonates (DAH)
           from shikimic acid based on silyl group migration
    • Abstract: Publication date: Available online 17 November 2018Source: Tetrahedron LettersAuthor(s): Jozef Gonda, Miroslav Psotka, Miroslava Martinková, Simona Fazekašová, Tatiana Mitríková, Mária Vilková The reaction of (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals with lower alcohols produced protected 3-deoxy-d-arabino-2-heptulosonates. The key transformation is based on an 1,4-O–O silyl group migration, followed by 6-exo-trig cyclisation to give the final pyranose.Graphical abstractGraphical abstract for this article
       
  • Synthesis of azabicyclo[n.1.0]alkane-derived bifunctional building blocks
           via the Corey–Chaykovsky cyclopropanation
    • Abstract: Publication date: Available online 17 November 2018Source: Tetrahedron LettersAuthor(s): Dmytro V. Yarmoliuk, Dmytro Serhiichuk, Vladyslav Smyrnov, Andriy V. Tymtsunik, Oleksandr V. Hryshchuk, Yuliya Kuchkovska, Oleksandr O. Grygorenko An efficient approach towards the synthesis of monoprotected azabicyclo[5.1.0]octane-derived conformationally restricted γ-amino acids and diamines is reported. Optimization of the conditions for the key Corey–Chaykovsky reaction allowed the construction of two isomeric methanoazepane frameworks on a multigram scale in 55–65% yield. Additionally, the developed approach was used in the three-step synthesis of 3,4-methano-β-proline and its diamine derivatives.Graphical abstractGraphical abstract for this article
       
  • δ-Azaproline : a versatile tool to design pseudopeptides by its
           incorporation via Nε or Nδ atoms
    • Abstract: Publication date: Available online 16 November 2018Source: Tetrahedron LettersAuthor(s): Olga Ovdiichuk, Lucie Flauder, Emelyne Humbert-Voss, Brigitte Jamart-Grégoire, Axelle Arrault δ-Azaproline, a bis-nitrogen proline, has been incorporated in pseudotripeptides of the type Xaa1-δazaPro-Xaa3. Peptide elongation via both nitrogen atoms has been explored by peptide coupling with glycine and/or alanine amino acids showing higher reactivity though an extra Nδ atom compare to the native Nε extremity. Carbonyls of some pseudopeptides have been converted into their thioanalogues. The conformational behavior of Gly-δazaPro-Gly tripeptide possessing thioamide linkages has been studied and compared with its carbonyl counterpart.Graphical abstractGraphical abstract for this article
       
  • Synthesis of Quaternary Succinimides Promoted by Ferric Nitrate
    • Abstract: Publication date: Available online 16 November 2018Source: Tetrahedron LettersAuthor(s): Cai-Ling Fan, Kuan Hu, Jing-Lin Wang, Xin-Qi Hao, Jun-Jie Wei, Mao-Ping Song, Chao Zheng An efficient protocol has been accomplished for the synthesis of quaternary α-aminosuccinimides in toluene medium involving 2-phenylimidazo[1, 2-a]pyridine in a one-pot reaction promoted by Ferric Nitrate at 120 oC. The protocol presented herein, is for the first time, via a novel transformation where Ferric Nitrate promotes imidazo[1,2-a]pyridine structural metamorphosis to the title compound quaternary succinimides. High compatibility, easy work-up, and excellent yields are the advantages of this protocol. The quaternary α-aminosuccinimides are expected to have great potential in synthesizing quaternary α-amino acids and applications in medicinal chemistry.Graphical abstractGraphical abstract for this article
       
  • Graphical abstract TOC
    • Abstract: Publication date: 5 December 2018Source: Tetrahedron Letters, Volume 59, Issue 49Author(s):
       
  • Graphical abstract TOC
    • Abstract: Publication date: 5 December 2018Source: Tetrahedron Letters, Volume 59, Issue 49Author(s):
       
  • Graphical abstract TOC cont’d
    • Abstract: Publication date: 5 December 2018Source: Tetrahedron Letters, Volume 59, Issue 49Author(s):
       
  • TsNBr2 promoted decarboxylative bromination of
           α,β-unsaturated carboxylic acids
    • Abstract: Publication date: Available online 14 November 2018Source: Tetrahedron LettersAuthor(s): Debojit Hazarika, Prodeep Phukan A rapid process for decarboxylative bromination of α,β-unsaturated carboxylic acids have been developed using N,N-dibromo-p-toluenesulfonamide (TsNBr2). Treatment of cinnamic acids with TsNBr2 in presence of potassium carbonate in acetonitrile produces corresponding β-bromostyrenes at room temperature. Exclusive formation of (E)-β-bromostyrenes was observed in a stereoselective manner within a very short period of time (5-15 min). This method was further extended for obtaining 1-bromoalkynes from corresponding propiolic acids. Instantaneous formation of bromoalkynes was observed when the reaction was carried out in presence of DBU as a base in acetonitrile at room temperature. A wide variety of cinnamic acids and propiolic acids could be converted to corresponding β-bromostyrenes and 1-bromoalkynes respectively under mild reaction condition with high to excellent yield.Graphical abstractGraphical abstract for this article
       
  • Formal [4+2] cycloaddition of 3-phenylcyclobutanones with nitriles
    • Abstract: Publication date: Available online 14 November 2018Source: Tetrahedron LettersAuthor(s): Emiko Igarashi, Kenta Sakamoto, Tomoyuki Yoshimura, Jun-ichi Matsuo Various 3-phenylcyclobutanones reacted with aliphatic and aromatic nitriles in the presence of Me3SiOTf to afford dihydropyridones by formal [4+2] cycloaddition.Graphical abstractGraphical abstract for this article
       
  • Recyclable CNT-Chitosan nanohybrid film utilized in copper-catalyzed
           aerobic ipso-hydroxylation of arylboronic acids in aqueous media
    • Abstract: Publication date: Available online 13 November 2018Source: Tetrahedron LettersAuthor(s): Han-Sem Kim, Sung-Ryu Joo, Ueon Sang Shin, Seung-Hoi Kim A convenient heterogeneous catalytic system consisting of recyclable and reusable carbon nanotube-chitosan nanohybrid film and copper salt was developed for the aerobic ipso-hydroxylation of arylboronic acids. A variety of arylboronic acids bearing electron-withdrawing or electron-donating groups were smoothly transformed at room temperature in water to afford the corresponding phenols in high yields.Graphical abstractGraphical abstract for this article
       
  • H+functionalization+toward+natural+product+synthesis”+[Tetrahedron+Lett+59+(2018)+188–202]&rft.title=Tetrahedron+Letters&rft.issn=0040-4039&rft.date=&rft.volume=">Corrigendum to “Recent topics in application of selective
           Rh(II)-catalyzed CH functionalization toward natural product synthesis”
           [Tetrahedron Lett 59 (2018) 188–202]
    • Abstract: Publication date: Available online 13 November 2018Source: Tetrahedron LettersAuthor(s): Takayuki Yakura, Hisanori Nambu
       
  • Suzuki-Miyaura cross-coupling reaction of monohalopyridines and L-aspartic
           acid derivative
    • Abstract: Publication date: Available online 13 November 2018Source: Tetrahedron LettersAuthor(s): Ayame Mikagi, Dai Tokairin, Toyonobu Usuki Suzuki-Miyaura cross-coupling reaction of halogenated pyridines and a borated L-aspartic acid derivative was conducted. The reactivity of chloro-, bromo-, and iodo-pyridines with substituents at the C2, C3, and C4 positions was investigated. Electron density of halogenated pyridines was also estimated by density functional theory (DFT) calculations. The order of experimental yield of halogen substituents was Br>I>>Cl and C3>C2, C4 whereas the DFT results indicated the reactivity order as I>>Br, Cl and C4>C2, C3. Optimized experimental conditions (3-bromopyridine) afforded the coupling product quantitatively.Graphical abstractGraphical abstract for this article
       
  • Cu-catalyzed Decarboxylative Iodination of Aryl Carboxylic Acids with NaI:
           A Practical Entry to Aryl Iodides under Aerobic Conditions
    • Abstract: Publication date: Available online 13 November 2018Source: Tetrahedron LettersAuthor(s): Zhengjiang Fu, Yongqing Jiang, Ligao Jiang, Zhaojie Li, Shengmei Guo, Hu Cai A simple and practical Cu-catalyzed decarboxylative iodination has been well established under aerobic condition, which provides a useful method to synthesize aryl iodides in moderate to good yields with the use of (hetero)aryl carboxylic acids and NaI as starting materials. Thiabendazole has been prepared via a three-step procedure to show synthetic practicability of the protocol.Graphical abstractGraphical abstract for this article
       
  • Propargylamine (secondary) as a building block in indole synthesis
           involving ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method:
           unexpected formation of (pyrazole)imine derivatives
    • Abstract: Publication date: Available online 13 November 2018Source: Tetrahedron LettersAuthor(s): Gangireddy Sujeevan Reddy, Suresh Babu Nallapati, P.S.V.K. Sri Saranya, B. Sridhar, Varadaraj Bhat Giliyaru, Raghu Chandrashekhar Hariharapura, G. Gautham Shenoy, Manojit Pal Propargylamine (secondary) has been explored as a building block in synthesizing indoles via an ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method. Indoles containing a pyrazole moiety at C-2 attached via the -CH2NH- linker (designed as potential anti-tubercular agents) were synthesized first and then generality / scope of the methodology was expanded by synthesizing other indoles. Unexpected formation of imine side products in first cases helped in synthesizing related (pyrazole)imines via a Cu catalyzed ultrasound assisted aerobic oxidation of precursor amines.Graphical abstractGraphical abstract for this article
       
  • Two xanthones and two rotameric (3⟶8) biflavonoids from the Cameroonian
           medicinal plant Allanblackia floribunda Oliv. (Guttiferae)
    • Abstract: Publication date: Available online 13 November 2018Source: Tetrahedron LettersAuthor(s): Bel Youssouf G. Mountessou, Joseph Tchamgoue, Jean Paul Dzoyem, Roland T. Tchuenguem, Frank Surup, Muhammad I. Choudhary, Ivan R. Green, Simeon F. Kouam Two xanthones, 2-(3-hydroxy-3,3-dimethyldihydroallyl)-dihydro-6-deoxyisojacareubin (1) and dihydro-6-deoxyjacareubin (2), and two 3⟶8 rotameric biflavonoids, (2R,3S)-volkensiflavone-7-O-β -acetylglucopyranoside (3) and (2S,3S)-morelloflavone-7-O- β -acetylglucopyranoside (4), together with fifteen known compounds, were isolated from a dichloromethane/methanol (1:1, v/v) extract of the bark of the plant Allanblackia floribunda. The structures of the new compounds were elucidated by NMR spectroscopy and mass spectroscopic techniques and those of the known ones were deduced by comparison with data reported in the literature. The isolated biflavonoids were obtained as mixtures of conformers exhibiting duplicate NMR signals in solution at 25 °C and their respective absolute configurations were assigned using circular dichroism spectroscopy. Selected isolated compounds were assessed for their antibacterial and antioxidant properties.Graphical abstractGraphical abstract for this article
       
  • Repurposing n-butyl stannoic acid as highly efficient catalyst for direct
           amidation of carboxylic acids with amines
    • Abstract: Publication date: Available online 12 November 2018Source: Tetrahedron LettersAuthor(s): Santoshkumar M. Potadar, Anil S. Mali, Krishnakant T. Waghmode, Ganesh U. Chaturbhuj This is the first-time report on the repurposing n-butyl stannoic acid as a catalyst for direct amidation of carboxylic acids with amines. Notably, efficient amidation observed in comparison with all other catalytic methods reported up until now. The protocol has successfully applied to the synthesis of a variety of amides. Moderate reaction parameters, clean amidation with excellent yields of desired amides, ability to tolerate a variety of functional groups, easy product isolation; commercial availability and recyclability of the catalyst are key advantages of the current protocol.Graphical abstractGraphical abstract for this article
       
  • Highly enantioselective aza-henry reaction of ketimines catalyzed by a
           chiral bifunctional thiourea-tertiary amine derived from quinine
    • Abstract: Publication date: Available online 22 October 2018Source: Tetrahedron LettersAuthor(s): Yanhong Fang, Ning Lu, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Haifeng Duan We have developed a highly enantioselective aza-Henry reaction of aryl α-ketoester-derived N-Ts ketimines with a wide range of substrate scope by a simpler bifunctional thiourea-tertiary amine catalyst derived from quinine. A variety of ketimines were investigated and corresponding products were obtained in excellent yields (up to 99% yield) with excellent enatioselectivities (up to 99% ee).Graphical abstractWe have developed a highly enantioselective aza-Henry reaction of aryl α-ketoester-derived N-Ts ketimines with a wide range of substrate scope by a simpler bifunctional thiourea-tertiary amine catalyst derived from quinine. The products were obtained in excellent yields (up to 99% yield) and good enantioselectivities (up to 99% ee).Graphical abstract for this article
       
  • Direct C(sp3)–H functionalization of 2-methylazaarenes
           Using 4-substituted-TEMPO
    • Abstract: Publication date: Available online 9 October 2018Source: Tetrahedron LettersAuthor(s): Chuanlei Zhu, Hongming Li, Changhu Chu An efficient and direct C(sp3)–H functionalization of 2-methyl azaarenes with persistent nitroxide radical 4-substituted-2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) under neutral conditions has been developed. A broad of 2-methylazaarenes could be reacted with 4-substituted TEMPOs to afford corresponding azaarene 2-methoxylamines by using cheaper copper (II) acetate hydrate as oxidant....Keywords: C(sp3)–H Functionalization, 2-Methylazaarenes, 4-substituted-TEMPO, azaarene 2-methoxylaminesGraphical abstractGraphical abstract for this article
       
  • Visible-Light-Induced Photocatalytic Difluoroalkylation of 3-Substituted
           Benzo[d]isoxazoles via Direct and Regioselective C-H Functionalization
    • Abstract: Publication date: Available online 5 October 2018Source: Tetrahedron LettersAuthor(s): Ming-Qing Hua, Fang-You Mou, Nian-Hong Wang, Yan Chen, Heng-Ying Xiong, Yan Huang, Cheng-Lin Lei, Qi Zhang The difluoroalkylation of unactivated benzo[d]isoxazoles with ethyl difluorobromoacetate by visible-light photoredox catalysis via direct and regioselective C-H functionalization has been efficiently achieved under mild reaction conditions. The difluoroalkylated adducts could be readily converted to a variety of corresponding CF2-containing heterocycles, demonstrating the synthetic utility of the present approach.Graphical abstractGraphical abstract for this article
       
  • A Jocic-type approach for a practical and scalable synthesis of
           pyrrolonaphthoxazepine (PNOX)-based potent proapoptotic agents
    • Abstract: Publication date: Available online 12 November 2018Source: Tetrahedron LettersAuthor(s): Stefano Federico, Tuhina Khan, Nicola Relitti, Giulia Chemi, Margherita Brindisi, Simone Brogi, Ettore Novellino, Daniela M. Zisterer, Giuseppe Campiani, Sandra Gemma, Stefania Butini We developed a Jocic-type protocol for the construction of the pyrrolonaphthoxazepine (PNOX) core. After an initial investigation based on the isolation of a trichloromethyl carbinol derivative, we shifted our attention towards a multicomponent single-step protocol. Screening of a variety of bases and solvents led to the identification of the optimum conditions for the preparation of the key α-aryloxy carboxylic acids to undergo intramolecular cyclization. The novel chemical route significantly improved overall yields for the preparation of PNOX-based compounds and was successfully extended to the preparation of 1,4-benzoxazinone-based templates.Graphical abstractGraphical abstract for this article
       
  • Quest for novel fluorogenic xanthene dyes: synthesis, spectral properties
           and stability of 3-imino-3H-xanthen-6-amine (pyronin) and its silicon
           analog
    • Abstract: Publication date: Available online 10 November 2018Source: Tetrahedron LettersAuthor(s): Anthony Romieu, Garance Dejouy, Ibai E. Valverde To expand the range of primary aniline fluorophores available and suitable for the design of fluorogenic protease probes, the synthesis of 3-imino-3H-xanthen-6-amine (known as pyronin) and its silicon analog (Si-pyronin) was explored and presented here. A comprehensive photophysical study of these two fluorescent anilines, confirms the effectiveness of the heteroatom-substitution approach (O→SiMe2) to yield dramatic red-shifts in absorption and fluorescence maxima of the xanthene scaffold (+85 nm). However, it also revealed its adverse effect on the hydrolytic stability of the Si-pyronin, especially at physiological pH. The pro-fluorescent character and utility of these two fluorogenic (hetero)xanthene dyes are also proved by the preparation and in vitro validation of activatable fluorescence “turn-on” probes for penicillin G acylase (PGA).Graphical abstractGraphical abstract for this article
       
  • Synthesis of Coumarin based Knoevenagel-Ugi Adducts by a sequential one
           pot Five-Component Reaction and their Biological evaluation as
           Anti-Bacterial agents
    • Abstract: Publication date: Available online 10 November 2018Source: Tetrahedron LettersAuthor(s): Sitanshu Kumar, Kapil Mukesh, Kusum Harjai, Vasundhara Singh An efficient multicomponent synthesis of Ugi compounds comprising coumarin backbone has been achieved by employing one pot five component sequential Knoevenagel-Ugi reaction. This method offers the advantages of easy handling procedure, atom economy, mild reaction conditions and good yields of products. A molecular library was synthesized by changing the substituents on two of the independent starting materials. The synthesized compounds were also tested for anti-microbial activities and were found to be moderate to good anti-bacterial agents.Graphical abstractGraphical abstract for this article
       
  • Stereocontrolled synthesis of four isomeric linoleate triols of relevance
           to skin barrier formation and function
    • Abstract: Publication date: Available online 10 November 2018Source: Tetrahedron LettersAuthor(s): Robert W. Davis, Alexander Allweil, Jianhua Tian, Alan R. Brash, Gary A. Sulikowski Linoleate triol esters are intermediates along the pathway of formation of the mammalian skin permeability barrier. In connection with the study of their involvement in barrier formation we required access to isomerically pure and defined samples of four linoleate triol esters. A common synthetic strategy was developed starting from isomeric alkynols derived from D-tartaric acid and 2-deoxy-D-ribose.Graphical abstractGraphical abstract for this article
       
  • Synthesis of dendritic bisphosphonates as bone targeting ligands
    • Abstract: Publication date: Available online 10 November 2018Source: Tetrahedron LettersAuthor(s): Kazuma Shimoda, Takahiro Mitsuoka, Kenta Ueda, Hiroshi Suemune, Go Hirai, Mariko Aso A dendritic bisphosphonate carrying three bisphosphonate (BP) units in close proximity was designed as a ligand to conjugate large therapeutic molecules for their bone selective delivery. The Bu3P-catalyzed conjugate addition of nitromethane to vinylidene bisphosphonate was effective to construct a quaternary carbon center carrying BP units. Owing to multivalent interactions, the dendritic bisphosphonate showed considerable affinity for the bone mineral hydroxyapatite even in the presence of a competitor, demonstrating potential as a bone targeting ligand.Graphical abstractGraphical abstract for this article
       
  • Synthesis of tetrahydroindolones and tetrahydrocarbazolones via palladium
           catalyzed C-H activation
    • Abstract: Publication date: Available online 10 November 2018Source: Tetrahedron LettersAuthor(s): Tiantian Zhang, Hongjin Xu, Chuanjun Song, Junbiao Chang The treatment of bromo homoallyl pyrrolyl/indolyl ketone derivatives with Pd(OAc)2 in the presence of PPh3 and Cs2CO3 in DMF resulted in the formation of tetrahydroindolones and tetrahydrocarbazolones in moderate to good isolated yields.Graphical abstractGraphical abstract for this article
       
  • Emericelactones A-D: Four novel polyketides produced by Emericella sp. XL
           029, a fungus associated the leaves of Panax notoginseng
    • Abstract: Publication date: Available online 10 November 2018Source: Tetrahedron LettersAuthor(s): Xue-Jiao Pang, Shuai-Bing Zhang, Hai-Li Chen, Wen-Ting Zhao, Deng-Feng Yang, Peng-Jie Xian, Lu-Lin Xu, Yan-Duo Tao, Hai-Yan Fu, Xiao-Long Yang The application of an OSMAC approach on an endophytic fungus Emericella sp. XL 029 has yielded four novel polyketides, emericelactones A-D (1-4).The structures and stereochemistry of 1-4 were elucidated by NMR and MS data analyses, computational methods, as well as by comparison with known compounds. Compound 1 contained an unprecedented linear pentaene substructure ending in an oxabicyclo[2.2.1]heptane moiety, while compounds 2-4 are epimers possessing an unprecedented linear triene structures ending in two cyclic moieties of an oxabicyclo[2.2.1]heptane and a cyclopentan-1-one. Compounds 1-4 showed moderate antimicrobial activities against three agricultural pathogenic fungi (Verticillium dahliae Kleb, Rhizoctonia solani and Gibberella saubinetii) and two human pathogenic bacteria (Micrococcus lysodeikticus and Salmonella typhi) with MIC values of 25-50 μg/mL.Graphical abstractGraphical abstract for this article
       
  • Direct alkylation of thiophenes via bis-coupling with vinyl
           acetates
    • Abstract: Publication date: Available online 10 November 2018Source: Tetrahedron LettersAuthor(s): Tong Zhang, Nai-Xing Wang, Yue-Hua Wu, Zhan Yan, Yalan Xing, Jia-Long Wen, Xue-Wang Gao A novel direct alkylation of thiophenes via bis-coupling with vinyl acetates has been developed. To the best of our knowledge, this represents the first report of the iron-catalysed coupling of two thiophenes with vinyl groups. Utilizing earth-abundant, inexpensive, and non-toxic iron catalysts, this methodology converts simple thiophenes to symmetrical dithienylethane derivatives under mild conditions in one step.Graphical abstractGraphical abstract for this article
       
  • Synthesis of 9-CD3-9-cis-Retinal Cofactor of
           Isorhodopsin
    • Abstract: Publication date: Available online 10 November 2018Source: Tetrahedron LettersAuthor(s): Mozhgan Navidi, Shreya Yadav, Andrey V. Struts, Michael F. Brown, Nasri Nesnas We report the synthesis of 9-CD3-9-cis-retinal via a six-step procedure from β-ionone. The steps involve an initial deuteration of the methyl ketone of β-ionone followed by two consecutive Horner-Wadsworth-Emmons (HWE) coupling reactions and their corresponding DIBAL reductions. A final oxidation of the allylic alcohol of the retinol leads to the target compound. This deuterium labeled retinoid is an important cofactor for studying protein-retinoid interactions in isorhodopsin.Graphical abstractGraphical abstract for this article
       
  • Symbiodinolactone A, a new 12-memberd macrolide from symbiotic marine
           dinoflagellate Symbiodinium sp.
    • Abstract: Publication date: Available online 9 November 2018Source: Tetrahedron LettersAuthor(s): Shin-ichiro Kurimoto, Yurika Iinuma, Jun'ichi Kobayashi, Takaaki Kubota A new 12-memberd macrolide, symbiodinolactone A, was isolated from the culture broth of symbiotic marine dinoflagellate Symbiodinium sp. The gross structure of symbiodinolactone A was elucidated by spectroscopic analyses, and the relative configuration was elucidated by the J-based configuration analysis and density-functional theory calculations. Symbiodinolactone A is the new 12-membered macrolide possessing an E double bond between C-4 and C-5, a branched methyl group at C-7, and a 1,2,3-trihydroxybutyl group at C-11. Symbiodinolactone A is the first usual size macrolide and the first non-nitrogen-containing macrolide from dinoflagellate Symbiodinium sp. Symbiodinolactone A might be generated by the unexplained dinoflagellate polyketide biosynthetic machinery.Graphical abstractGraphical abstract for this article
       
  • New borrelidin derivatives from an endophytic Streptomyces sp.
    • Abstract: Publication date: Available online 9 November 2018Source: Tetrahedron LettersAuthor(s): Li Zhang, Jing Shi, Cheng Li Liu, Lang Xiang, Shi Ying Ma, Wei Li, Rui Hua Jiao, Ren Xiang Tan, Hui Ming Ge Three new borrelidin-type macrolactones, designated as borrelidins J−L (4−6), together with borrelidin A (1), borrelidin E (2), and 12-desnitrile-12-carboxyl-borrelidin (3) were isolated from a plant endophytic Streptomyces sp. NA06554. Their structures were determined by extensive spectroscopic analysis including HRESIMS, 1D and 2D NMR data. The antibacterial activities for compounds 1−6 were examined. Borrelidins A (1) and L (6) showed potent and moderate antibacterial activity against Micrococcus luteus, respectively, whereas other derivatives (2−5) are almost inactive, which allows us to propose a plausible structure-activity relationship.Graphical abstractGraphical abstract for this article
       
  • [1],+[5]diazocine-3,8-diones+via+the+reaction+of+3-aminopyrazolone+with+benzaldehyde+derivatives&rft.title=Tetrahedron+Letters&rft.issn=0040-4039&rft.date=&rft.volume=">PTSA catalyzed synthesis of functionalized dipyrazolo[1],
           [5]diazocine-3,8-diones via the reaction of 3-aminopyrazolone with
           benzaldehyde derivatives
    • Abstract: Publication date: Available online 9 November 2018Source: Tetrahedron LettersAuthor(s): Mohammad Reza Khodabakhshi, Firouz Matloubi Moghaddam, Mostafa Kiamehr A simple procedure for the synthesis of dipyrazolo[1], [5]diazocine-3,8-diones was developed via the one-pot reaction of 3-aminopyrazolone with substituted benzaldehydes in the presence of catalytic p-toluenesulfonic acid (PTSA).Graphical abstractGraphical abstract for this article
       
  • Ishigadine A, a new canthin-6-one alkaloid from an Okinawan marine sponge
           Hyrtios sp.
    • Abstract: Publication date: Available online 9 November 2018Source: Tetrahedron LettersAuthor(s): Hideaki Takahashi, Shin-ichiro Kurimoto, Jun'ichi Kobayashi, Takaaki Kubota A new indole alkaloid with the canthin-6-one skeleton, ishigadine A, has been isolated from an Okinawan marine sponge Hyrtios sp. The structure of ishigadine A was elucidated on the basis of spectroscopic analyses. Ishigadine A is a new canthin-6-one alkaloid possessing a hydroxy group, a 1,3-dimethyl-4-methylthioimidazolium, and 1-propylguanidine. Ishigadine A is the third canthin-6-one alkaloid from sponges. Ishigadine A might be generated from L-arginine, L-histidine, and L-tryptophan. Ishigadine A exhibited moderate cytotoxicity against L1210 murine leukemia cells.Graphical abstractGraphical abstract for this article
       
  • New Synthesis of Imidazole Derivatives from Cyanobenzenes
    • Abstract: Publication date: Available online 9 November 2018Source: Tetrahedron LettersAuthor(s): Maxime Beuvin, Maxime Manneveau, Sonia Diab, Baptiste Picard, Morgane Sanselme, Serge R. Piettre, Julien Legros, Isabelle Chataigner An efficient access to 4-aryl imidazole scaffolds is described in two steps and one operation. Cyanoaryl-imidazolines are easily obtained by a (3+2) heterocyloaddition involving cyanobenzenes as dipolarophiles and a non-stabilized azomethine ylide as an electron-rich 1,3-dipole. Oxidation of the crude mixture affords an efficient two-steps access to the corresponding imidazoles.Graphical abstractGraphical abstract for this article
       
  • Formal total synthesis of enigmazole A
    • Abstract: Publication date: Available online 9 November 2018Source: Tetrahedron LettersAuthor(s): Andreas Meissner, Takayuki Kishi, Yuka Fujisawa, Yuto Murai, Hiroyoshi Takamura, Isao Kadota A stereoselective formal total synthesis of enigmazole A, a marine macrolide isolated from cinachyrella enigmatica, is described. Lewis acid mediated intramolecular allylation of an α-acetoxy ether, prepared from alcohol and carboxylic acid fragments was carried out to construct the methylene THP ring with high stereoselectivity. The late-stage macrolactonization of the corresponding seco-acid provided a known synthetic intermediate of enigmazole A.Graphical abstractGraphical abstract for this article
       
  • Stachyodin A, a pterocarpan derivative with unusual spirotetrahydrofuran
           ring from the roots of Indigofera stachyodes
    • Abstract: Publication date: Available online 8 November 2018Source: Tetrahedron LettersAuthor(s): Yun-Feng Zhang, Zhi-Xiang Zhu, Hui Sun, Hui-Na Yao, Xiao-Nan Chen, Li Liu, Shi-Lin Zhang, Yun-Fang Zhao, Peng-Fei Tu, Jun Li Stachyodin A (1), a rearrangement product of pterocarpan featuring a 6/5/5/6 tetracyclic ring system with an unusual spirotetrahydrofuran ring, and stachyodin B (2), a new dihydrochalcone, along with five known analogues (3−7) were isolated from the roots of Indigofera stachyodes. The structures of 1 and 2 were elucidated on the basis of their HRESIMS and NMR spectroscopic data, and their absolute configurations were determined by X-ray crystallographic analysis and electronic circular dichroism (ECD) data, respectively. Compounds 2–4 showed inhibition of nitric oxide production in lipopolysaccharide-activated BV-2 microglial cells.Graphical abstractGraphical abstract for this article
       
  • Synthesis and stereoselective evaluation of a (1R)-(–)-myrtenal-derived
           pseudo C2 -symmetric dodecaheterocycle as a potential heterofunctional
           chiral auxiliary
    • Abstract: Publication date: Available online 8 November 2018Source: Tetrahedron LettersAuthor(s): Anahí C. Sánchez-Chávez, Ma. Elena Vargas-Díaz, Julio C. Ontiveros-Rodríguez, Salvador Pérez-Estrada, Gustavo G. Flores-Bernal, Daniel Mendoza-Espinosa, Alejandro Álvarez-Hernández, Francisco Delgado, Joaquín Tamariz, L. Gerardo Zepeda-Vallejo The synthesis and diastereoselective performance of the pseudo C2-symmetric dodecaheterocycle 3 in nucleophilic and electrophilic reactions are reported. Compound 3 proved to be a highly diastereoselective template to generate a pair of enantiomeric moieties within its structure in a programmed manner. Hence, this study describes the synthesis of a novel potential heterobifunctional chiral auxiliary.Graphical abstractGraphical abstract for this article
       
  • Synthesis of trans 8-substituted-6-phenyl-6,7,8,9-tetrahydro-3H-pyrazolo
           [4,3–f]isoquinolines using a Pictet-Spengler approach
    • Abstract: Publication date: Available online 8 November 2018Source: Tetrahedron LettersAuthor(s): Andrew Bailey, Andrew Lister, Thomas Moss, James S. Scott, Ye Wu, Scott G. Lamont In the following communication we report two complementary approaches for the synthesis of trans 8-substituted-6-phenyl-6,7,8,9-tetrahydro-3H-pyrazolo[4,3–f]isoquinolines. The first method, directly from α-methyl substituted indazole ethanamines, was successful but had limited substrate scope. The second method utilised a modified Pictet-Spengler cyclisation reaction on an aniline substrate followed by late stage construction of the indazole ring and was more versatile in terms of substrate scope.Graphical abstractGraphical abstract for this article
       
  • Highly Regioselective Dehexanoylation in Fully Hexanoylated Flavonoids
    • Abstract: Publication date: Available online 8 November 2018Source: Tetrahedron LettersAuthor(s): Zhiwei Zheng, Ziyi Han, Li Cai, Dandan Zhou, Bryson R. Chavis, Changsheng Li, Qiang Sui, Kaiyuan Jiang, Qi Gao Highly selective removal of the 7-O-hexanoyl group in fully hexanoylated flavones, isoflavones, flavanone, and flavonol was achieved under mild conditions using K2CO3 in a 1:1 mixture of CH3OH–CH2Cl2. The resulting 7-OH flavonoids are valuable intermediates for the synthesis of flavonoid 7-O-glycosides via phase-transfer-catalyzed (PTC) glycosylation.Graphical abstractGraphical abstract for this article
       
  • Ruthenium Dihydride Complexes as Enyne Metathesis Catalysts
    • Abstract: Publication date: Available online 8 November 2018Source: Tetrahedron LettersAuthor(s): Martin A. Dolan, Alexandre D.C. Dixon, John D. Chisholm, Daniel A. Clark Ruthenium–catalyzed enyne metathesis is a reliable and efficient method for the formation of 1,3-dienes, a common structural motif in synthetic organic chemistry. The development of new transition-metal complexes competent to catalyze enyne metathesis reactions remains an important research area. This report describes the use of ruthenium (IV) dihydride complexes with the general structure RuH2Cl2(PR3)2 as new catalysts for enyne metathesis. These ruthenium (IV) dihydrides have been largely unexplored as catalysts in metathesis-based transformations. The reactivity of these complexes with 1,6 and 1,7-enynes was investigated. The observed reaction products are consistent with the metathesis activity occurring through a ruthenium vinylidene intermediate.Graphical abstractGraphical abstract for this article
       
  • An investigation into the role of 2,6-lutidine as an additive for the
           RuCl3-NaIO4 mediated oxidative cleavage of olefins to ketones
    • Abstract: Publication date: Available online 7 November 2018Source: Tetrahedron LettersAuthor(s): David W. Watson, Matthew Gill, Paul Kemmitt, Scott G. Lamont, Mihai V. Popescu, Iain Simpson 2,6-Lutidine has been identified as a beneficial additive for the oxidative cleavage of olefins to ketones by NaIO4 in the presence of catalytic RuCl3, improving the yield and shortening the reaction times. In the absence of 2,6-lutidine reactions stalled at the diol intermediate with incomplete conversion to the desired ketones. The reaction protocol described herein also avoids the use of harmful solvents such as CCl4 and DCE and is tolerant of a range of functional groups.Graphical abstractGraphical abstract for this article
       
  • Synthesis of dipyrrolo[2,3-a:1’,2’,3’-fg]acridin-12(1H)-ones
    • Abstract: Publication date: Available online 7 November 2018Source: Tetrahedron LettersAuthor(s): Renée L. Beyer, Hakan Kandemir, Mohan Bhadbhade, Ibrahim F. Sengul, Chao-wei Leu, Daniel Wenholz, Naresh Kumar, David StC. Black Acylation reactions of 4,6-dimethoxyindoles with glyoxyloyl chlorides were achieved by the use of graphite powder in 1,2-dichloroethane at reflux. The products were monoketones as a result of decarbonylation, rather than the expected 1,2-diketones. Treatment of these monoketones with base led to their cyclisation and elimination of methanol to afford the novel dipyrrolo[2.3-a:1’,2’,3’-fg]acridin-12(1H)-ones.Graphical abstractGraphical abstract for this article
       
  • A Telescoped Knochel-Hauser / Kumada-Corriu Coupling Strategy to
           Functionalized Aromatic Heterocycles
    • Abstract: Publication date: Available online 7 November 2018Source: Tetrahedron LettersAuthor(s): Kyle Clagg, Sara Hold, Archana Kumar, Stefan G. Koenig, Remy Angelaud The direct application of Knochel-Hauser derivative arylmagnesium halides in Kumada-Corriu couplings is described. By utilizing the in situ-generated Grignard reagents, the transmetalation with stoichiometric zinc salts to known Negishi coupling conditions is avoided, thereby streamlining the transformation. Several aromatic hetereocycles participate in the deprotonation and couple with a variety of phenyl iodides and bromides in isolated yields up to 81%. The parent system is demonstrated on 6 g scale with 79% yield, and monitored via ReactIR to show the stability of the Grignard and progression of the deprotonation / C-C coupling reaction.Graphical abstractGraphical abstract for this article
       
  • L-Proline catalyzed domino Michael addition of N-substituted anilines
    • Abstract: Publication date: Available online 5 November 2018Source: Tetrahedron LettersAuthor(s): Mohit L. Deb, Bhaskar Deka, Iftakur Rahman, Pranjal K. Baruah Here we report L-proline catalyzed 3-component reaction of indoles, aldehydes and N-substituted anilines in water as solvent at room temperature for the synthesis of 3-(α,α-diarylmethyl)indoles. The reaction is in fact a Michael addition of N-substituted anilines to alkylideneindolenines. The reaction is very clean, high yielding and having broad substrate scope. A tentative mechanism is proposed.Graphical abstractGraphical abstract for this article
       
  • Cooperative Ion Pair Receptor Based on Tolan as a Li+/HSO4 - Selective
           Extractor and Fluorescent Indicator
    • Abstract: Publication date: Available online 5 November 2018Source: Tetrahedron LettersAuthor(s): Min-Sung Ko, Adil S. Aslam, Dong-Gyu Cho A new tolan derivative was synthesized as a selective ion pair receptor for LiHSO4. The observed ion pair selectivity was accomplished by introducing aza-12-crown-4, which is size-selective for Li+. The ion pair receptor can function as an extractor and fluorescent indicator for LiHSO4.Graphical abstractGraphical abstract for this article
       
  • Viscosity Measurements Using a Two-photon Ratiometric Fluorescent Sensor
           with Two Rotors
    • Abstract: Publication date: Available online 5 November 2018Source: Tetrahedron LettersAuthor(s): Fei Liu, Yeshen Luo, Meiying Xu A new ratiometric two-photon fluorescence sensor, Qca-Cy2, comprised of a hybrid cyanine–carbazole platform with two rotating sites is described. Qca-Cy2 can report on mitochondrial viscosity within live cells, as well as in living tissues at depths of 50-130 μm by ratiometric fluorescence imaging using two-photon microscopy.Graphical abstractQca-Cy2 is comprised of a hybrid cyanine–carbazole platform with two rotating sites. Qca-Cy2 can report on mitochondrial viscosity within live cells, as well as in living tissues at depths of 50-130 μm by ratiometric fluorescence imaging using two-photon microscopy.Graphical abstract for this article
       
  • A New Route to Synthesis of Substituted Pyrazoles through Oxidative [3+2]
           Cycloaddition of Electron Deficient Alkenes and Diazocarbonyl Compounds
    • Abstract: Publication date: Available online 5 November 2018Source: Tetrahedron LettersAuthor(s): J. Paul Raj, D. Gangaprasad, K. Karthikeyan, R. Rengasamy, M. Kesavan, M. Venkateswarulu, M. Vajjiravel, J. Elangovan A collection of 3,5-disubstituted pyrazoles are constructed by the oxidative [3+2] cycloaddition of electron deficient terminal olefins with α-diazoesters and amides in the presence of Oxone and cetyltrimethyl ammoinum bromide. The highlights of this protocol are; (i) shorter reaction time (ii) moderate to excellent yield (iii) good regioselectivity.Graphical abstractA collection of 3,5-disubstituted pyrazoles are constructed by the oxidative [3+2] cycloaddition of electron deficient terminal olefins with α-diazoesters and amides in the presence of Oxone and cetyltrimethyl ammoinum bromide. The highlights of this protocol are; (i) shorter reaction time (ii) moderate to excellent yield (iii) good regioselectivity.Graphical abstract for this article
       
  • Testing the Veracity of Claims of Lewis Acid Catalysis
    • Abstract: Publication date: Available online 5 November 2018Source: Tetrahedron LettersAuthor(s): Ivan Šolić, Hong Xuan Lin, Roderick W. Bates Are reactions employing Lewis acids really catalysed by those Lewis acids, or by “hidden Brønsted acids”, i.e. Brønsted acids generated in situ by hydrolysis? Testing of a series of reactions using Sc(III), Fe(III), In(III) and Y(III) by addition of 2,6-di-t-butyl-4-methylpyridine reveal that all are likely to follow the latter pathway. A reaction claimed to be catalysed by CBr4 through halogen bonding is also likely to be Brønsted acid catalysed.Graphical abstractGraphical abstract for this article
       
  • UV light enabled methylation of quinoline-2-thione using dimethyl
           sulfoxide to give quinoline methyl sulfide
    • Abstract: Publication date: Available online 5 November 2018Source: Tetrahedron LettersAuthor(s): Tong-Lin Wang, Xiao-Jun Liu, Xi Zhang, Bao-Qian Cao, Zheng-Jun Quan, Xi-Cun Wang An UV-light-induced S-methylation of quinoline-2-thione was completed by using dimethyl sulfoxide as methyl reagent. A series of quinoline methyl sulfides were prepared in moderate to good yields under environmentally friendly and mild conditions.Graphical abstractGraphical abstract for this article
       
  • [1],+[3],+[5]-triazines&rft.title=Tetrahedron+Letters&rft.issn=0040-4039&rft.date=&rft.volume=">Synthesis and transformations of pyrrolo[1,2-a][1], [3], [5]-triazines
    • Abstract: Publication date: Available online 3 November 2018Source: Tetrahedron LettersAuthor(s): Jonas Verhoeven, B. Narendraprasad Reddy, Lieven Meerpoel, Jan Willem Thuring, Guido Verniest Pyrrolotriazines and related fused azaheterocycles have high potential for the synthesis of bioactive compounds, especially as a purine base isoster in carbon linked nucleosides. Although many structurally related compounds have already been synthesized and used in medicinal chemistry, pyrrolo[1], [3], [5]triazines have barely been described. The present work describes the synthesis of such heterocycles via condensation of 2-amino-3-ethoxycarbonylpyrrole with ethoxycarbonyliso(thio)cyanate. In a brief reactivity study of the obtained fused pyrroles, O- and S-alkylation, ester hydrolysis as well as regioselective bromination at the 6-position was demonstrated.Graphical abstractGraphical abstract for this article
       
  • Base Catalysed Diastereoselective Tamura Cycloaddition of Vinylidene
           Indanediones
    • Abstract: Publication date: Available online 2 November 2018Source: Tetrahedron LettersAuthor(s): Ravikiran Donthi, Venkatram R. Reddy, Sivakumar N. Reddy, Rajesh Chandra The base catalysed Tamura cycloaddition reaction of vinylidene indanediones afforded the corresponding spiro[indane-1,3-dione-1-tetralone] structures as single diastereomers in excellent yields. Chiral bifunctional hydrogen bonding thiourea catalysts rendered the reaction enantioselective. However, the selectivity observed was moderate with Soós catalyst providing an enantiomeric ratio of 82.5:17.5.Graphical abstractGraphical abstract for this article
       
  • A truncated palytoxin analogue, palytoxin carboxylic acid, isolated as an
           insecticidal compound from the red alga, Chondria armata
    • Abstract: Publication date: Available online 2 November 2018Source: Tetrahedron LettersAuthor(s): Shoko Mori, Kohtaro Sugahara, Mitsuru Maeda, Keiko Shimamoto, Takashi Iwashita, Tohru Yamagaki Palytoxin (PTX) has been widely studied owing to its outstanding toxic properties and complex structural features. It is a great challenge to identify and isolate analogues of PTX from various organisms and reveal their physiological activities. We previously reported the isolation of PTX as an insecticidal compound from the red alga, Chondria armata. In this study, we investigate another active compound from C. armata, which has similar toxicity and chromatographic behavior as PTX. Our detailed structural analysis reveals that this compound is palytoxin carboxylic acid. We characterized its physicochemical properties and conducted extensive NMR studies. This analogue has a structure devoid of the terminus of PTX, such that its presence in the alga implies the role of symbiotic microorganisms in marine ecosystems.Graphical abstractGraphical abstract for this article
       
  • Transition metal-free regioselective access to 9,10-dihydroanthracenes via
           the reaction of anthracenes with elemental phosphorus in the KOH/DMSO
           system
    • Abstract: Publication date: Available online 2 November 2018Source: Tetrahedron LettersAuthor(s): Vladimir A. Kuimov, Nina.K. Gusarova, Svetlana F. Malysheva, Boris A. Trofimov Anthracene and its 9- or 9,10-substituted (Me, Ph, Cl, Br) derivatives react with red phosphorus (Pn) in the KOH/DMSO superbase system at 85-120 °C to afford 9,10-dihydroanthracenes in good to excellent yields, thus providing simple and clean access to these extensively used dihydroaromatics.Graphical abstractGraphical abstract for this article
       
  • Silica gel-mediated hydrohalogenation of unactivated alkenes using
           hydrohalogenic acids under organic solvent-free conditions
    • Abstract: Publication date: Available online 1 November 2018Source: Tetrahedron LettersAuthor(s): Kiyoshi Tanemura Silica gel-mediated hydrochlorination of unactivated alkenes using 35% hydrochloric acid under organic solvent-free conditions proceeded to give the corresponding chlorides in good yields. Hydrobromination or hydriodination using 47% hydrobromic acid or 55% hydriodic acid afforded the corresponding halides, respectively. Silica gel could be recycled five times without any significant loss of activities.Graphical abstractGraphical abstract for this article
       
  • Cluster glycosides and heteroglycoclusters presented in alternative
           arrangements
    • Abstract: Publication date: Available online 31 October 2018Source: Tetrahedron LettersAuthor(s): Andreza S. Figueredo, Luis O.B. Zamoner, Martin Rejzek, Robert A. Field, Ivone Carvalho Multivalent carbohydrates, or glycoclusters, are useful tools to study glycan-lectin and glycan-enzyme recognition processes and have wide potential therapeutic applicability. Herein, we report the synthesis of novel glycoclusters presenting glucopyranose units in alternate arrangements by coupling through the C-1, C-2, C-3 or C-6 sugar positions and using tetra- and hexa-valent scaffolds for multivalent display. Coupling the appropriate azide-functionalised d-glucopyranose units with alkynlated penta- or dipenta-erythritol central cores was accomplished via copper-catalysed azide-alkyne cycloaddition (CuAAC), yielding a panel of eight tetra- and hexa-valent glycoclusters in good yields (52-83%). This click chemistry strategy was extended to the preparation of four heteroglycoclusters using a tris(hydroxymethyl)-aminomethane (TRIS) central scaffold. One unit of either the conventional 1-deoxy-d-nojirymicin iminosugar or its’ C-5 epimeric l-gulo isomer, were incorporated along with three d-glucopyranose units linked through either C-1 or C-6.Graphical abstractGraphical abstract for this article
       
  • Cholesterol degradation in archaeological pottery mediated by fired clay
           and fatty acid pro-oxidants
    • Abstract: Publication date: Available online 31 October 2018Source: Tetrahedron LettersAuthor(s): Simon Hammann, Mathilda Whittle, Lucy J.E. Cramp, Richard P. Evershed Cholesterol is generally absent in animal fat residues preserved in archaeological ceramic vessels. It is known from edible oil refining that during bleaching with activated clay sterols are degraded, largely via oxidation. Laboratory heating experiments using fired clay from replica pottery vessels promoted rapid degradation of cholesterol via oxidation. Furthermore, heating cholesterol with fatty acids (saturated and unsaturated) revealed additional degradation to occur independently of the ceramic matrix. As both conditions are met in archaeological pottery during animal (and plant) product processing involving heating, the very rare detection of sterols in organic residues can be explained.Graphical abstractGraphical abstract for this article
       
  • Aggregation-induced emission enhancement (AIEE)-active
           mechanofluorochromic tetraphenylethene derivative bearing a rhodamine unit
           
    • Abstract: Publication date: Available online 31 October 2018Source: Tetrahedron LettersAuthor(s): Ya Yin, Fei Zhao, Zhao Chen, Gang Liu, Shouzhi Pu A novel tetraphenylethene derivative with a rhodamine unit was successfully synthesized via high-efficiency Suzuki coupling reaction. The highly solid-state emissive target fluorescent molecule exhibited significative aggregation-induced emission enhancement (AIEE) feature. Furthermore, the luminogen showed reversible mechanochromic luminescence behavior involving color change from orange to red. In addition, the powder X-ray diffraction (XRD) test results verified that the mechanofluorochromic phenomenon of luminogen 1 was attributed to a morphological transformation between the crystalline and amorphous states.Graphical abstractGraphical abstract for this article
       
  • Hydrazides of glycine-containing decasubstituted pillar[5]arenes:
           Synthesis and encapsulation of Floxuridine
    • Abstract: Publication date: Available online 31 October 2018Source: Tetrahedron LettersAuthor(s): Dmitriy N. Shurpik, Denis A. Sevastyanov, Pavel V. Zelenikhin, Evgenia V. Subakaeva, Vladimir G. Evtugyn, Yuriy N. Osin, Peter J. Cragg, Ivan I. Stoikov Hydrazides of glycine-containing decasubstituted pillar[5]arenes were synthesized and characterized. Dynamic light scattering (DLS) and transmission electron microscopy (TEM) showed that self-assembly into monodisperse spherical nanoparticles (28 nm) was typical in water for pillarene hydrazides containing glycylglycide fragments (1 × 10−3 M). Binding of the antitumor drug Floxuridine in water by the substituents of the macrocycle was established by NMR spectroscopy. It was shown by DLS and TEM, that heating the macrocycle-Floxuridine system in a 1:1 ratio at 1 × 10−4 M led to its self-organization into monodisperse spherical particles 132 nm in diameter.Graphical abstractGraphical abstract for this article
       
  • Synthesis of both enantiomers of conosilane A
    • Abstract: Publication date: Available online 30 October 2018Source: Tetrahedron LettersAuthor(s): Hironori Okamura, Naoki Mori, Hidenori Watanabe, Hirosato Takikawa Conosilane A, an inhibitor of 11β-hydroxysteroid dehydrogenase type 1 isolated from Conocybe siliginea, is a tremulane sesquiterpene with highly oxygenated tetracyclic ring system. In this study, we report the synthesis of both enantiomers of conosilane A. The key steps of this synthesis involve asymmetric aldol reaction, furan-ring oxidation followed by transacetalization and intramolecular reductive Heck-type cyclization.Graphical abstractGraphical abstract for this article
       
  • Photocatalytic aerobic cross-coupling reaction of N-substituted anilines
           with N-aryl glycine esters: synthesis of α-aryl α-amino esters
    • Abstract: Publication date: Available online 30 October 2018Source: Tetrahedron LettersAuthor(s): Bin Sun, Jiacheng Deng, Deyu Li, Can Jin, Weike Su A novel photocatalytic cross dehydrogenative coupling reaction of N-aryl glycine esters with N-substituted anilines has been developed. The reaction proceeds effectively using methylene blue as a photocatalyst under visible light irradiation without any metal, chemical oxidant or additive. A variety of α-aryl α-amino derivatives were prepared in moderate to excellent yields with a high para-regioselectivity.Graphical abstractGraphical abstract for this article
       
  • Efficient Synthesis of Highly Functionalized Indole and Phenol Containing
           3,3’-Disubstituted Oxindoles and Chromene Fused Spirooxindoles
    • Abstract: Publication date: Available online 29 October 2018Source: Tetrahedron LettersAuthor(s): Nandarapu Kumarswamyreddy, Kanduru Lokesh, Venkitasamy Kesavan 3-Alkynyl-3-OBoc oxindoles underwent Cu(II) mediated Friedel-Crafts alkylation with indoles and phenols to yield of structurally diverse 3-alkynyl-3-indole/phenol-oxindole derivatives. The synthetic application of alkylated phenol derivatives was further demonstrated to biologically important new class of chromene fused spirooxindoles through intramolecular metal-free iodocyclization under mild reaction conditions with broad substrate scope in very good yields.Graphical abstractGraphical abstract for this article
       
  • One-Pot Synthesis of Tertiary Alkyl Fluorides from Methyl Oxalates by
           Radical Deoxyfluorination under Photoredox Catalysis
    • Abstract: Publication date: Available online 29 October 2018Source: Tetrahedron LettersAuthor(s): Julien Brioche Tertiary alkyl fluorides have been prepared from methyl oxalates derived from tertiary alcohols by a sequential one-pot hydrolysis/photoredox catalyzed radical deoxyfluorination sequence. The reaction operates under mild conditions and tolerates a wide range of functional groups. This method provides an alternative approach to ionic deoxyfluorination transformations for the incorporation of Carbone–Fluorine quaternary centers into organic molecules.Graphical abstractGraphical abstract for this article
       
  • Organocatalytic ring-opening polymerization of L-lactide in supercritical
           carbon dioxide under plasticizing conditions
    • Abstract: Publication date: Available online 29 October 2018Source: Tetrahedron LettersAuthor(s): Nobuyuki Mase, Moniruzzaman, Shunsuke Mori, Jun Ishizuka, Fumihiro Kumazawa, Shoji Yamamoto, Kohei Sato, Tetsuo Narumi The synthesis of poly-L-lactide (PLLA) in supercritical carbon dioxide (scCO2) was accomplished using an organocatalyst. The reaction proceeded smoothly under CO2 plasticizing polymerization conditions at a lower temperature than those conventionally employed. This method allowed the formation of high-molecular-weight, pure PLLA, and therefore has the potential to reduce energy consumption and minimize production costs. Our method is non-toxic and efficient, affording a high-quality product while complying with volatile organic compound regulations. We can produce PLLA that meets the increasing standards (safety and high functionality) of the medical sector, while being applicable to full-scale industrial manufacturing and academic research.Graphical abstractGraphical abstract for this article
       
  • A New BODIPY-Based Fluorescent “Turn-On” Probe for Highly Selective
           and Rapid Detection of Mercury Ions
    • Abstract: Publication date: Available online 29 October 2018Source: Tetrahedron LettersAuthor(s): Baocheng Zhou, Siyao Qin, Bo Chen, Yifeng Han A new fluorescent sensor based on the BODIPY fluorophore and the carboxyl-thiol metal bonding receptor for Hg2+ was designed and synthesized. The sensor is highly selective for Hg2+ (about 630-fold fluorescence enhancement) over relevant competing metal ions, sensitive to ppb levels of Hg2+ (with detection limit of 5.7 nM), and fast response toward Hg2+ (within 30 seconds) in aqueous solution.Graphical abstractGraphical abstract for this article
       
  • Ultrasound-assisted green one-pot synthesis of linked bis-heterocycle
           peptidomimetics via IMCR/post-transformation/tandem strategy
    • Abstract: Publication date: Available online 28 October 2018Source: Tetrahedron LettersAuthor(s): Bhavna Kaveti, Sandra C. Ramírez-López, Rocío Gámez Montaño The sequential aligning of two eco-friendly and powerful tools for the synthesis of peptidomimetics resulted in the rapid generation of molecular complexity in target molecules. We herein report a versatile IMCR/post-transformation/tandem synthetic strategy that emphasizes the special role of orthogonal bifunctional reagents in isocyanide based multicomponent reactions (IMCR) to generate a synthetic platform for subsequent heterocyclization reactions. This is the first one-pot synthesis of a 2,5-diketopiperazine linked to a 1,4-disubstituted 1,2,3-triazole. The Ugi-4CR/lactamization/click sequence is facile, mild, atom-economical, and green. The present work contributes to the green and one-pot synthesis of bis-heterocycle peptidomimetics and design of new bioactive molecules.Graphical abstractGraphical abstract for this article
       
  • Synthesis and Application of Phosphonothioates, Phosphonodithioates,
           Phosphorothioates, Phosphinothioates and Related Compounds
    • Abstract: Publication date: Available online 26 October 2018Source: Tetrahedron LettersAuthor(s): David J. Jones, Eileen M. O'Leary, Timothy P. O'Sullivan Methods for the preparation of phosphonothioates, phosphonodithioates, phosphorothioates, phosphinothioates and related compounds are reviewed. The application of these compounds as synthetic intermediates is also discussed.Graphical abstractGraphical abstract for this article
       
  • I2/Fe(NO3)3·9H2O-catalyzed oxidative synthesis of aryl carboxylic acids
           from aryl alkyl ketones and secondary benzylic alcohols
    • Abstract: Publication date: Available online 26 October 2018Source: Tetrahedron LettersAuthor(s): Liang Xu, Yingying Chen, Zhenlu Shen, Yuru Wang, Meichao Li An interesting and convenient procedure for the oxidative transformation of aryl alkyl ketones and secondary benzylic alcohols to aryl carboxylic acids has been developed. By using iodine and Fe(NO3)3·9H2O as the catalysts, DMSO and oxygen as the oxidants, the desired aryl carboxylic acids were synthesized in moderate to excellent yields (up to 91%).Graphical abstractGraphical abstract for this article
       
  • Transition Metal Free One Pot Synthesis of Aryl Carboxylic Acids via
           Dehomologative Oxidation of Styrenes
    • Abstract: Publication date: Available online 26 October 2018Source: Tetrahedron LettersAuthor(s): Bhausaheb N. Patil, Pratima A. Sathe, Babasao S. Parade, Kamlesh S. Vadagaonkar, Atul C. Chaskar Iodine/NaOH-catalyzed one-pot dehomologative oxidation of styrenes to aryl carboxylic acids has been reported. A wide range of carboxylic acids are obtained using iodine (I2) as a catalyst, tert-butyl hydroperoxide (TBHP) as an oxidant and sodium hydroxide (NaOH) as a base. This reliable conversion involves dehomologation of styrene to aromatic aldehyde which on subsequent oxidation affords aryl carboxylic acid. This protocol was used for gram-scale synthesis as it is free from chromatographic purification. This is the first report for the oxidative transformation of styrenes into aryl carboxylic acids under transition metal-free conditions.Graphical abstractGraphical abstract for this article
       
  • A concise stereoselective synthesis of Pterosin B
    • Abstract: Publication date: Available online 25 October 2018Source: Tetrahedron LettersAuthor(s): Hannah R. Dexter, Esther Allen, David M. Williams Pterosin B is a naturally occurring indanone found in bracken fern (Pteridium aquilinum) that displays a variety of interesting pharmacological properties, but for which few stereoselective syntheses exist. Herein we describe a 7-step stereoselective synthesis of (2R)-pterosin B via 6-bromo-5,7-dimethylindan-1-one whose structure was confirmed by NOE analysis and structure determination by X-ray crystallography. The hydroxyethyl chain was introduced via a Suzuki-Miyaura cross-coupling reaction. The 2-methyl group was introduced stereoselectively by methylation of a SAMP [(S)-1-amino-2-methoxymethyl)pyrrolidine] hydrazone and the chiral auxiliary was removed to produce (2R)-pterosin B. The structure of pterosin B was confirmed by specific rotation and structural determination by X-ray crystallography.Graphical abstractGraphical abstract for this article
       
  • Synthetic Studies Toward Bicyclic Endoperoxides Presenting Polar Side
           Chains
    • Abstract: Publication date: Available online 25 October 2018Source: Tetrahedron LettersAuthor(s): Sandra Gemma, Luisa di Cerbo, Nicola Relitti, Alessandra Vallone, Margherita Brindisi, Simone Brogi, Giulia Chemi, Ettore Novellino, Giuseppe Campiani, Stefania Butini We developed a synthetic strategy for the preparation of tetrahydrofuro[2,3-c][1,2]dioxane and 2,3,8-trioxa[3,3,1]nonanes bearing polar functional groups at C3 and C4, respectively. The synthetic strategy has been applied to the synthesis of 2,3,8-trioxa[3,3,1]nonanes bearing various amides and amines at C3 useful for structure-activity relationships investigation as antiplasmodial compounds. The synthesis of 1 and the reaction conditions identified for its conversion to amides and amines could pose the basis for the use of this class of endoperoxides also in conjugation with other drugs for polypharmacology approaches.Graphical abstractGraphical abstract for this article
       
  • Convenient one-pot formation of highly functionalized
           5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL
           inhibitors
    • Abstract: Publication date: Available online 25 October 2018Source: Tetrahedron LettersAuthor(s): Julien R.C. Prevost, Arina Kozlova, Bouazza Es Saadi, Esra Yildiz, Sara Modaffari, Didier M. Lambert, Lionel Pochet, Johan Wouters, Eduard Dolusic, Raphaël Frédérick Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents could be easily prepared by a rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or inconvenient reagents such as elemental halogens. These useful products can serve as starting materials for other reactions or as pharmacologically interesting compounds. In our work we have shown that the resulting 5-bromothiazole compounds could lead to monoacylglycerol lipase (MAGL) inhibition in the μM range.Graphical abstractThe present study describes the optimization of a new method of synthesis of highly functionalized 5-bromo-2-amino-1,3-thiazoles by a rapid and efficient one-pot method, using simple starting materials and mild conditions. Interestingly some of the synthesized compounds demonstrate promising monoacylglycerol lipase inhibition properties.Graphical abstract for this article
       
  • Synthesis of α-hydroxyalkyl dehydroazepanes via catalytic
           enantioselective borylative migration of an enol nonaflate
    • Abstract: Publication date: Available online 25 October 2018Source: Tetrahedron LettersAuthor(s): Helen A. Clement, Dennis G. Hall A Pd-catalyzed borylative migration methodology for cyclic enol perfluorosulfonates was applied to the synthesis of the corresponding 7-membered, azepane ring system. Throughout the optimization, it was shown that the reaction is sensitive to the nitrogen protecting group as well as the type of base and solvent. The resulting cyclic allylboronate reacts stereoselectively with aldehydes for the synthesis of novel α-hydroxyalkyl dehydroazepanes in good yield and enantioselectivity over two steps. We highlight the utility of this methodology with an efficient synthesis of the de novo 7-membered ring analogue of the piperidine alkaloid β-conhydrine.Graphical abstractGraphical abstract for this article
       
  • Synthesis of 2-Phosphonylated Imidazo[1,2-a]pyridines under
           Catalyst-Free Conditions
    • Abstract: Publication date: Available online 25 October 2018Source: Tetrahedron LettersAuthor(s): Aleksandr S. Krylov, Ksenia I. Kaskevich, Elena B. Erkhitueva, Nataly I. Svintsitskaya, Albina V. Dogadina A series of novel 2-phosphonylated imidazo[1,2-a]pyridines was accessed from C–N coupling of chloroethynylphosphonates and commercially available N-unsubstituted 2-aminopyridines. The product yield depends on the nature and position of the substituent in the pyridine ring.Graphical abstractGraphical abstract for this article
       
  • Isolation of indole alkaloid and anthranilic acid derivatives from Indigo
           Pulverata Levis
    • Abstract: Publication date: Available online 25 October 2018Source: Tetrahedron LettersAuthor(s): Kyoung Jin Park, Dong Hyun Kim, Chung Sub Kim, Joonseok Oh, Lalita Subedi, Mi Won Son, Sang Zin Choi, Sun Yeou Kim, Kang Ro Lee A new indole alkaloid, pulveratinol (1), and two new anthranilic acid derivatives (2 and 3) were isolated from Indigo Pulverata Levis, together with 12 known compounds (4–15). The structures of the new compounds (1–3) were determined through spectroscopic methods. The absolute configuration of 1 was confirmed further by electronic circular dichroism (ECD) data analysis and computational method with advanced statistics (DP4). All isolated compounds (1–15) were evaluated for their potential neuroprotective effects through induction of nerve growth factor (NGF) in C6 glioma cells.Graphical abstractGraphical abstract for this article
       
  • Synthesis of unique dimethyl thiazoline containing intermediate of novel
           PPARδ agonists
    • Abstract: Publication date: Available online 25 October 2018Source: Tetrahedron LettersAuthor(s): Tara Man Kadayat, Geumwoo Lee, Kyungjin Jung, Hee-Jong Hwang, Jeongmin Joo, Dongyup Hahn, Hayoung Hwang, Keun-Gyu Park, Sung Jin Cho, Kyung-Hee Kim, Jungwook Chin Peroxisome proliferator-activated receptor delta (PPARδ) is considered as a promising biological target for the development of new drugs to treat metabolic syndrome including hyperlipidemia. In this study, a simple and efficient method for the preparation of a unique dimethyl thiazoline containing intermediate (13) of new PPARδ agonists as GW501516 analogue is described. The intermediate 13 was readily obtained by coupling reaction of 4-(chloromethyl)-5,5-dimethyl-2-(4-(trifluoromethyl)phenyl)-4,5-dihydrothiazole (11) with 4-mercapto-2-methylphenol (12) in the presence of tetrabutylammonium hydrogensulfate (TBAHS) and Cs2CO3 in DMF at 80 °C for 1 h. This unique intermediate could be useful for the synthesis of various novel PPARδ agonists to understand the structural and biological significance of PPARδ.Graphical abstractGraphical abstract for this article
       
  • Parallel Strategies for the Synthesis of Annulated Pyrido[3,4-b]indoles
           via Rh(I)- and Pd(0)-Catalyzed Cyclotrimerization
    • Abstract: Publication date: Available online 25 October 2018Source: Tetrahedron LettersAuthor(s): Bianca M. Saliba, Satyam Khanal, Michael A. O'Donnell, Kathryn E. Queenan, Junho Song, Matthew R. Gentile, Seann P. Mulcahy Two different pathways for the synthesis of annulated pyrido[3,4-b]indoles are reported using metal-catalyzed cyclotrimerization reactions. A stepwise process using Rh(I)-catalysis in the final step of the synthesis and a multicomponent, tandem catalytic approach using Pd(0)-catalysis both lead to complex nitrogen-containing heterocycles in good yields. Substituent effects are investigated for both pathways, demonstrating that the Pd(0)-catalyzed approach is more sensitive to electron-withdrawing groups.Graphical abstractGraphical abstract for this article
       
  • Ethyl 5-trichloromethyl-1,2,4-oxadiazole-3-carboxylate as a versatile
           building block in medicinal chemistry
    • Abstract: Publication date: Available online 25 October 2018Source: Tetrahedron LettersAuthor(s): Žiga Jakopin A straightforward route for preparing derivatives of ethyl 5-trichloromethyl-1,2,4-oxadiazole-3-carboxylate, in which the 5-trichloromethyl and/or the ester functionalities are displaced by various nucleophiles, has been designed. Mild reaction conditions were chosen to enable the formation of products, which constitute a new series of bifunctional 3,5-disubstituted 1,2,4-oxadiazole building blocks capable of being integrated into biologically relevant molecules.Graphical abstractGraphical abstract for this article
       
  • Synthesis of noval chiral tridentate amino alcohols as chiral solvating
           agents under ball-milling conditions
    • Abstract: Publication date: Available online 24 October 2018Source: Tetrahedron LettersAuthor(s): Si Feng, Liangyuan Yao, Fengliang Liu, Xiao Zeng, Junjie Wang A new family of chiral solvating agents based on chiral didentate amino alcohols and chloromethyl pyridine derivatives were synthesized by ball milling in solvent free condition. The new chiral tridentate amino alcohols were tested as chiral NMR solvating agents for the Ts-derivatives of amino acids, other several acids and pyrazole drugs. For the Ts-derivatives of amino acids studied herein, chiral tridentate amino alcohol 3a could be used for the assignment of the absolute configurations of their racemes through the chemical shift non-equivalences of their CH3 (Ts) protons with certain confidence.Graphical abstractGraphical abstract for this article
       
  • A coumarin based highly selective fluorescent chemosensor for sequential
           recognition of Cu2+ and PPi
    • Abstract: Publication date: Available online 23 October 2018Source: Tetrahedron LettersAuthor(s): Xianjiao Meng, Duanlin Cao, Zhiyong Hu, Xinghua Han, Zhichun Li, Dong Liang, Wenbing Ma In this study, we have successfully synthesized a new coumarin based fluorescent chemosensor 1, in which tren and quinolone are introduced as receptors for sequential recognition of Cu2+ and PPi. The structure of chemosensor 1 was characterized by 1H NMR, 13C NMR and ESI-HR-MS. Sensor 1 showed an obvious “on-off” fluorescence quenching response toward Cu2+, and the quenching efficiency reached a maximum of 99.6% with the addition of 20 equiv. of Cu2+. The 1-Cu2+ complex showed an “off-on” fluorescence enhancement response toward PPi over many competitive anions, especially HPO42- and H2PO4-. The detection limit of sensor 1 was 1.9 ×10-6 M to Cu2+ and 5.96×10-8 M to PPi. In addition, sensor 1 showed a 1: 1 binding stoichiometry to Cu2+ and sensor 1-Cu2+ showed a 2: 1 binding stoichiometry to PPi in CH3CN/HEPES buffer medium (9: 1 v/v, pH=7.4). The stable pH range of sensor 1 to Cu2+ and 1-Cu2+ to PPi was from 4 to 8.Graphical abstractGraphical abstract for this article
       
  • Synthesis of a New Coumarin Dye for pH Independent Staining of Lysosomes
    • Abstract: Publication date: Available online 23 October 2018Source: Tetrahedron LettersAuthor(s): Rui Zhu, Siyu Wang, Xinhui Su, Jian Liu A novel coumarin analogue, synthesized from 2-formylcinnamic acid and resorcinol via acid catalyzed condensation and intramolecular rearrangement, is used for pH-independent staining of lysosome in live cells via lysosomal esterase mediated fluorogenic deacetylation.Graphical abstractGraphical abstract for this article
       
 
 
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