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Tetrahedron Letters
Journal Prestige (SJR): 0.683
Citation Impact (citeScore): 2
Number of Followers: 119  
 
  Hybrid Journal Hybrid journal (It can contain Open Access articles)
ISSN (Print) 0040-4039 - ISSN (Online) 1359-8562
Published by Elsevier Homepage  [3163 journals]
  • Recent application of acidic 1,3-azolium salts as promoters in the
           solution-phase synthesis of nucleosides and nucleotides
    • Authors: Masaki Tsukamoto; Kin-ichi Oyama
      Pages: 2477 - 2484
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Masaki Tsukamoto, Kin-ichi Oyama
      Acidic 1,3-azolium salts are prepared from Brønsted acids and 1,3-azoles such as imidazole, thiazole, and oxazole. Acidic imidazolium salts are frequently employed as promoters for the synthesis of nucleotides using the phosphoramidite method in a solution phase. Recently, it was revealed that thiazolium and oxazolium salts catalyzed Vorbrüggen-type N-glycosylation reactions to give nucleosides. These reactivities are attributed to the stronger Brønsted acidities of the thiazolium and oxazolium salts relative to those of the imidazolium salts. This digest focuses on recent progress in the applicability of acidic 1,3-azolium salts as promoters in the solution-phase synthesis of nucleosides and nucleotides.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.03.074
       
  • Strategic innovations for the synthesis of vinigrol
    • Authors: Vipul V. Betkekar; Krishna P. Kaliappan
      Pages: 2485 - 2501
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Vipul V. Betkekar, Krishna P. Kaliappan
      Since the isolation of unique tricyclic diterpenoid vinigrol, its promising biological activities and complex framework have resulted in numerous synthetic efforts to the total synthesis of this venerable molecule for the past two and half decades. This mini review highlights the significance of various synthetic strategies towards this structurally unique and challenging natural product.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.049
       
  • An efficient HCl promoted Petasis reaction of 2-pyridinecarbaldehydes,
           amines and 1,2-oxborol-2(5H)-ols
    • Authors: Tao Ding; Yazhen Duan; Hui Li; Baoguo Zhao; Jun Yang
      Pages: 2502 - 2505
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Tao Ding, Yazhen Duan, Hui Li, Baoguo Zhao, Jun Yang
      A Petasis reaction of 2-pyridinecarbaldehydes with various amines and 4-substituted 1,2-oxaborol-2(5H)-ols was developed. In the presence of HCl, the reaction proceeded smoothly under very mild conditions and the corresponding desired products were obtained in medium to excellent yields. This method allows the access a wide range of highly functionalized allylic alcohols, which might be useful compounds in medicinal and material chemistry.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.04.013
       
  • Synthesis of substituted phenols via 1,1-dichloro-2-nitroethene promoted
           condensation of carbonyl compounds with DMF
    • Authors: Fukai Wang; Wei Wu; Xiaoyong Xu; Xusheng Shao; Zhong Li
      Pages: 2506 - 2510
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Fukai Wang, Wei Wu, Xiaoyong Xu, Xusheng Shao, Zhong Li
      A novel and efficient metal-free synthesis of phenolic compounds was developed via coupling cyclization of DMF as a carbon source with active methylene compounds such as 1,3-dicarbonyl compounds with the assistance of 1,1-dichloro-2-nitroethene. The method we used was different from other traditional phenol functionalization methods. In the reaction, the 1,1-dichloro-2-nitroethene as a promoter which unlike our previous research on 1,1-dichloro-2-nitroethene. The method allows the convenient construction of phenolic compounds under mild reaction conditions and moderate yields.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.04.076
       
  • A highly efficient TEMPO mediated oxidation of sugar primary alcohols into
           
    • Authors: Varsha Tiwari; Vishnu Nayak Badavath; Adesh Kumar Singh; Jeyakumar Kandasamy
      Pages: 2511 - 2514
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Varsha Tiwari, Vishnu Nayak Badavath, Adesh Kumar Singh, Jeyakumar Kandasamy
      Oxidation of various sugar primary alcohols into corresponding uronic acids was demonstrated using 1-chloro-1,2-benziodoxol-3(1H)-one and TEMPO. The reaction proceeds at room temperature in good to excellent yields. Primary alcohols get oxidized selectively over the secondary alcohols under mild reaction conditions.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.021
       
  • Hydrogen bond surrogate stabilized water soluble 310-helix from a
           disordered pentapeptide containing coded α-amino acids
    • Authors: Sunit Pal; Erode N. Prabhakaran
      Pages: 2515 - 2519
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Sunit Pal, Erode N. Prabhakaran
      Replacing a hypothetical i + 3 → i peptide H-bond in a disordered pentapeptide, that lacks any helicogenic Cα-tetrasubstituted residues, with a propyl linker and carbamylating the N-terminal nitrogen constrains it in the elusive 310-helical structure with high helicity and stability under varying conditions of temperature and pH, confirmed by NMR and CD analyses.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.029
       
  • I2/TBHP promoted oxidative C–N bond formation at room temperature:
           Divergent access of 2-substituted benzimidazoles involving ring distortion
           
    • Authors: Moumita Saha; Asish R. Das
      Pages: 2520 - 2525
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Moumita Saha, Asish R. Das
      A new ‘one pot’ tandem synthesis of 2-substituted benzimidazoles has been developed from 2-aminobenzyl alcohol/2-aminobenzamide and different coupling partners (nitriles, aldehydes and 1,3-diketones) via iodine and TBHP promoted oxidative ring contraction. The present strategy involves sequential C–N bond formation, cyclization, subsequent ring contraction and dehydrogenation to afford various medicinally important benzimidazole derivatives in moderate to good yields. This operationally simple synthetic approach proceeds at room temperature under base-free condition, broadly applicable to a wide array of nitriles and aldehydes bearing oxidation prone functional groups and noteworthy to mention that various acyclic 1,3-diketonesundergo selective C–C bond cleavage leading to 2-alkyl benzimidazoles under mild condition.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.028
       
  • Palladium catalyzed Heck-arylation/cyclization cascade: An environmentally
           benign and efficient synthesis of 4-arylcoumarins in water
    • Authors: Junmin Chen; Wei Liu; Liandi Zhou; Yongli Zhao
      Pages: 2526 - 2531
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Junmin Chen, Wei Liu, Liandi Zhou, Yongli Zhao
      An environmentally benign and efficient approach for the synthesis of 4-arylcoumarins from ortho-hydroxy cinnamate ester derivatives with aryl iodides was developed in water under aerobic conditions. This transformation proceeds through a palladium catalyzed Heck-arylation/cyclization cascade reaction. The present protocol features a wide substrate scope and readily available starting materials to afford the desired products in high to excellent yields.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.032
       
  • Stellatolide H, a cytotoxic peptide lactone from a deep-sea sponge
           Discodermia sp.
    • Authors: Shohei Nakamukai; Kentaro Takada; Kazuo Furihata; Yuji Ise; Shigeru Okada; Yasuhiro Morii; Nobuhiro Yamawaki; Tomohiro Takatani; Osamu Arakawa; Kirk R. Gustafson; Shigeki Matsunaga
      Pages: 2532 - 2536
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Shohei Nakamukai, Kentaro Takada, Kazuo Furihata, Yuji Ise, Shigeru Okada, Yasuhiro Morii, Nobuhiro Yamawaki, Tomohiro Takatani, Osamu Arakawa, Kirk R. Gustafson, Shigeki Matsunaga
      Stellatolide H (1) was isolated from a deep-sea sponge Discodermia sp. as the cytotoxic constituent. The planar structure of 1 was elucidated on the basis of the NMR spectroscopic and mass spectrometric data. The absolute configurations of the constituent amino acid residues were determined by the Marfey’s method. Stellatolide H (1) is a peptide lactone of the callipeltin class with its N-terminus blocked by 3-hydroxy-6,8-dimethyldeca-(4Z,6E)-dienoic acid (Hdda).
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.033
       
  • Ruthenium-catalyzed nitrogen-directed ortho CH borylation of aromatic
           imines with pinacolborane
    • Authors: Yuna Maeda; Masaru Sato; Shinsuke Okada; Miki Murata
      Pages: 2537 - 2540
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Yuna Maeda, Masaru Sato, Shinsuke Okada, Miki Murata
      An efficient ruthenium catalyst system for the direct ortho CH borylation of aromatic imines is described. The reaction of tert-butyl-1-arylmethanimines with pinacolborane in the presence of Ru(cod)(cot), followed by hydrolysis, to afford the ortho-formyl-substituted arylboronates. The borylation was achieved with complete mono-selectivity.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.038
       
  • 1-D copper(I) coordination polymer based on bidentate 1,3-dithioether
           ligand: Novel catalyst for azide-alkyne-cycloaddition (AAC) reaction
    • Authors: Sankar Saha; Kinkar Biswas; Basudeb Basu
      Pages: 2541 - 2545
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Sankar Saha, Kinkar Biswas, Basudeb Basu
      A novel 1,3-bis(4-fluorophenylthio)-propane ligand based CuI 1-D polymeric coordination complex having formula ([(CuI)2{ArS(CH2)3SAr}2]n, Ar = 4-F-C6H4) has been synthesized and characterized by 1H NMR, 13C NMR and single crystal XRD techniques. This complex has been employed for the first time as suitable catalyst for base-free one-pot three-component regioselective azide-alkyne cycloaddition (AAC) reaction. A novel 1,2,3-triazole compound with sulfur functionalized pendant arms has also been prepared using our catalytic system in a multicomponent manner via one-pot two-step reaction.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.040
       
  • Regioselective oxidative ring-opening of cyclopropenyl carboxylates by
           visible light photoredox catalysis
    • Authors: Qianwen Ye; Hongqiang Ye; Dongping Cheng; Xiaonian Li; Xiaoliang Xu
      Pages: 2546 - 2549
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Qianwen Ye, Hongqiang Ye, Dongping Cheng, Xiaonian Li, Xiaoliang Xu
      Catalyzed by Ir(dFCF3ppy)2(dtbbpy)PF6, several aroyl methylidenemalonates were synthesized in good to excellent yields via visible light photoredox-catalyzed the oxidative ring-opening of cyclopropenyl carboxylate derivatives. The possible mechanism of oxidative quenching cycle was proposed.
      Graphical abstract image

      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.047
       
  • Thiazonaphthalimide derivatives: Synthesis and interaction with DNA
    • Authors: Alexandra Botz; Yves Chenavier; Jacques Pécaut; Pascale Delangle; Christelle Gateau
      Pages: 2550 - 2553
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Alexandra Botz, Yves Chenavier, Jacques Pécaut, Pascale Delangle, Christelle Gateau
      The synthesis of several thiazonaphthalimide derivatives is described. The exclusive formation of angular rather than linear isomers was unequivocally demonstrated by NMR and single crystal X-ray diffraction. Their photophysical properties and ability to bind calf-Thymus DNA with affinities in the range of 104 makes them interesting candidates to probe DNA by fluorescence.
      Graphical abstract image

      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.052
       
  • Direct selenation of imidazoheterocycles and indoles with selenium powder
           in a copper-catalyzed three-component one-pot system
    • Authors: Tao Guo; Zhe Dong; Panke Zhang; Weiqin Xing; Liping Li
      Pages: 2554 - 2558
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Tao Guo, Zhe Dong, Panke Zhang, Weiqin Xing, Liping Li
      An efficient and convenient Cu-catalyzed three-component reaction is described for the selenation of imidazoheterocycles/indoles with Se powder and aryl iodides. This procedure provides diverse 3-arylselenylimidazoheterocycles and 3-arylselenylindoles with good yields and functional group tolerance. Some of the products exhibited better or comparable antiproliferative activities compared with the positive control 5-fluorouracil against H1975, PC-9, HGC-27, EC-109, and MCF-7 cancer cell lines.
      Graphical abstract image

      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.046
       
  • A novel plant growth regulator from Pholiota lubrica
    • Authors: Arif Yanuar Ridwan; Ryuta Matoba; Jing Wu; Jae-Hoon Choi; Hirofumi Hirai; Hirokazu Kawagishi
      Pages: 2559 - 2561
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Arif Yanuar Ridwan, Ryuta Matoba, Jing Wu, Jae-Hoon Choi, Hirofumi Hirai, Hirokazu Kawagishi
      Nine compounds including a new cinnamamide (1), N-(1-cinnamoylpyrrolidin-2-yl)cinnamamide, and two compounds (8 and 9) first isolated from natural sources, were obtained from the edible mushroom Pholiota lubrica. Their structures were determined by the interpretation of spectroscopic data. Compounds 1, 3 and 9 exhibited the inhibitory activity against lettuce, while compounds 2 and 7 promoted the growth of lettuce.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.045
       
  • Palladium-catalyzed C–H alkenylation of quinoxaline N-oxide enabled by a
           mono-N-protected amino acid
    • Authors: Márcia Silvana Freire Franco; Murilo Helder de Paula; Paulina Cecylia Glowacka; Fernando Fumagalli; Giuliano Cesar Clososki; Flavio da Silva Emery
      Pages: 2562 - 2566
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Márcia Silvana Freire Franco, Murilo Helder de Paula, Paulina Cecylia Glowacka, Fernando Fumagalli, Giuliano Cesar Clososki, Flavio da Silva Emery
      The efficient alkenylation of quinoxaline N-oxide was achieved via Pd-catalyzed C–H activation, using the assistance of a mono-N-protected amino acid. Further deoxygenation of the 2-styrylquinoxaline-N-oxides yielded the corresponding styrylquinoxaline derivatives.
      Graphical abstract image

      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.054
       
  • A simple approach for the synthesis of azocine alkaloids: The total
           synthesis of megallanesine
    • Authors: Prajesh S. Volvoikar; Santosh G. Tilve
      Pages: 2567 - 2569
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Prajesh S. Volvoikar, Santosh G. Tilve
      A new three step synthetic route to construct azocine ring system using anion chemistry and intramolecular Friedel-Craft reaction of an ester is presented. This method allows synthesis of azocine ring analogues in excellent overall yields. The designed strategy was applied for the synthesis of naturally occurring magallanesine.
      Graphical abstract image

      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.055
       
  • Synthesis and biological evaluation of 12-, 13-, 14-membered macrolides
           and open chain 2,6-trans-disubstituted dihydropyran analogues for
           aspergillides
    • Authors: Srihari Pabbaraja; Naresh Gantasala; Sridhar Ydhyam; Hari Krishna Namballa; Subhashini Gundeboina; Mallikharjuna R. Lambu; Sanjeev Meena; Dipak Datta
      Pages: 2570 - 2576
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Srihari Pabbaraja, Naresh Gantasala, Sridhar Ydhyam, Hari Krishna Namballa, Subhashini Gundeboina, Mallikharjuna R. Lambu, Sanjeev Meena, Dipak Datta
      Stereoselective synthesis of twenty (three 12-, five 13- and twelve 14-membered) macrolides and seventeen functionalized 2,6-trans-disubstituted dihydropyran derivatives have been achieved. The key reactions include an Achmatowicz rearrangement, Ferrier-type alkynylation, Yamaguchi macrolactonization and Lindlar’s hydrogenation. Biological screening of the synthesised compounds showed moderate activity against human cancer cell-lines.
      Graphical abstract image

      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.056
       
  • Njaoamine I, a cytotoxic polycyclic alkaloid from the Haplosclerida sponge
           Haliclona (Reniera) sp.
    • Authors: Carlos Urda; Marta Pérez; Jaime Rodríguez; Rogelio Fernández; Carlos Jiménez; Carmen Cuevas
      Pages: 2577 - 2580
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Carlos Urda, Marta Pérez, Jaime Rodríguez, Rogelio Fernández, Carlos Jiménez, Carmen Cuevas
      A new cytotoxic polycyclic alkaloid containing a quinoline moiety, njaoamine I (1) has been isolated from the methanol extract of the sponge Haliclona (Reniera) sp. collected at Okuza Island, Tanzania. The structure of compound 1 was determined by 1D and 2D NMR and HRMS data analysis. Its relative configuration was elucidated by a NOESY experiment and confirmed by comparison of its NMR spectral data to those of njaoamines A–H. Moreover, njaoamine G (2) was also detected by LC/MS analysis of the methanol extract. Njaoamine I (1) displays cytotoxic activity against a panel of three human tumor cell lines in the micromolar range.
      Graphical abstract image

      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.059
       
  • A novel fluorescent probe with a large stokes shift for cysteine based on
           dicyanoisophorone
    • Authors: Jiaqi Hou; Pengfei Cai; Chengyun Wang; Yongjia Shen
      Pages: 2581 - 2585
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Jiaqi Hou, Pengfei Cai, Chengyun Wang, Yongjia Shen
      In this work, a dicyanoisophorone-based turn-on fluorescent probe, DCIP, for highly selective and sensitive detection of cysteine was designed based on nucleophilic substitution mechanism. Moreover, compared with typical cysteine probes, DCIP showed great selectivity and sensitivity for cysteine over other amino acids including the similar structured homocysteine (Hcy) and glutathione (GSH). Further, the detection limit toward cysteine was calculated to be as low as 0.70 μM. In addition, the utility of DCIP as a bioanalytical molecular tool was demonstrated by fluorescence imaging of biothiols in living cells.
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.057
       
  • Microwave assisted alkylation of
           ortho-methyl-tetra-C-naphthyl-resorcinarene and its phosphorylated
           derivatives with haloalkanes and ethyl bromoacetate
    • Authors: Olga S. Serkova; Valentina V. Glushko; Maria A. Egorova; Vera I. Maslennikova
      Pages: 2586 - 2589
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Olga S. Serkova, Valentina V. Glushko, Maria A. Egorova, Vera I. Maslennikova
      Tetra- and octa-phosphinanyl-ortho-methyl-tetra-C-naphthyl-resorcinarenes were alkylated with haloalkanes and ethyl bromoacetate. In all cases, the reactions followed the Michaelis-Arbuzov pathway to give phosphonates with haloalkyl groups at the periphery of the molecule. The O-alkylation of tetra-phosphato-ortho-methyl-tetra-C-naphthyl-resorcinarene with ethyl bromoacetate afforded a derivative with different functional sites at the horizontal and vertical benzene rings of the macrocycle, that is, phosphate and ethyl acetate sites, respectively. The exhaustive O-alkylation of ortho-methyl-tetra-C-naphthyl-resorcinarene afforded the octa(ethyl acetate) derivative, which was quantitatively transformed into the corresponding acid and amide.
      Graphical abstract image

      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.062
       
  • Asymmetric organocatalytic α-amination of 2-oxindoles with
           bis(2,2,2-trichloroethyl)azo-dicarboxylate
    • Authors: Mattia Bondanza; Gennaro Pescitelli; Alessandro Mandoli
      Pages: 2590 - 2594
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Mattia Bondanza, Gennaro Pescitelli, Alessandro Mandoli
      An enantioselective electrophilic amination of 3-substituted-2-oxindoles is reported, using bis(2,2,2-trichloroethyl)azo-dicarboxylate and commercially available Cinchona alkaloid organocatalysts. The best results were obtained in the reaction of 3-aryl substrates, with high to excellent yields (75% to quantitative) and good stereoselectivity (64–77% ee). Facile reductive conversion of the protected 3-hydrazino fragment into the corresponding primary amine was also demonstrated, to expand the synthetic flexibility of asymmetric electrophilic amination with azo-dicarboxylic esters en route to enantioenriched 3-amino-2-oxindoles. The absolute configuration of 3-amino-3-phenyl-2-oxindole was independently established by electronic circular dichroism (ECD), combined with time-dependent density functional theory (TDDFT).
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      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.063
       
  • The Castagnoli-Cushman reaction in a three-component format
    • Authors: Evgeny Chupakhin; Dmitry Dar'in; Mikhail Krasavin
      Pages: 2595 - 2599
      Abstract: Publication date: 27 June 2018
      Source:Tetrahedron Letters, Volume 59, Issue 26
      Author(s): Evgeny Chupakhin, Dmitry Dar'in, Mikhail Krasavin
      The first example of the Castagnoli-Cushman reaction of homophthalic acid with an amine and an aldehyde conducted in a three-component format is reported. This new protocol employs no dehydrating agents and, unlike the traditional Castagnoli-Cushman reaction of homophthalic anhydride, allows simultaneous mixing of all three reagents and provides good to excellent yields of trans-configured tetrahydroisoquinolonic acids.
      Graphical abstract image

      PubDate: 2018-06-05T15:43:23Z
      DOI: 10.1016/j.tetlet.2018.05.066
       
  • Recent advances in chemoselective acylation of amines
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Francesca Piazzolla, Andrea Temperini
      N-chemoselective acylation of amines in the presence of competing nucleophiles, like alcohols and thiols, is by no means a simple achievement in organic synthesis and even more difficulties arise when distinctions between primary, secondary, and aromatic amines need to be made. The present digest will review some recent achievements in this field, ranging from transamidation reactions to carboxylic acid derivatives transacylations. In addition, more creative strategies, involving chemoenzymatic reactions and metal-catalyzed acylations and carbonylations, will be discussed in order to furnish a concise view of the state-of-the-art approaches to this synthetic challenge.
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      PubDate: 2018-06-11T08:18:36Z
       
  • Base-promoted 1,3-dipolar cycloaddition reaction of nitrile oxides with
           methyl 1,4-dioxo-1,4-dihydronaphthalene-2-carboxylate for the construction
           of naphtho[2,3-d]isoxazole-4,9(3aH,9aH)-diones
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Yong You, Yong-Zheng Chen, Xiao-Mei Zhang, Xiao-Ying Xu, Wei-Cheng Yuan
      A base mediated 1,3-dipolar cycloaddition reaction of methyl 1,4-dioxo-1,4-dihydronaphthalene-2-carboxylate with nitrile oxides in situ generated from N-hydroximoyl chlorides was achieved. With this developed protocol, a range of structurally diverse naphtho[2,3-d]isoxazole-4,9(3aH,9aH)-dione derivatives were smoothly obtained in high yields (up to 95%) with up to >20:1 regioselectivities and >20:1 diastereoselectivities under mild conditions. The promising applicability of the protocol was also demonstrated by the further transformations.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Concise semisynthesis of novel phenazine-vitamin E hybrids via
           regioselective tocopheryl ortho-quinone formation
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Guillaume Viault, Jean-Jacques Helesbeux, Pascal Richomme, Denis Séraphin
      A regioselective method for the semisynthesis of phenazine derivatives has been disclosed through an efficient IBX mediated ortho-quinone formation from vitamin E derivatives. High chemo- and regio-selectivity was observed during the oxidation step and the corresponding 5,6-ortho-quinones could react with various phenylenediamines. Thus, this methodology proves its interest as a concise semisynthetic pathway to phenazine-vitamin E hybrids with moderate to good yields.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • DMAP catalysed vinylogous Rauhut–Currier reaction of allenoates with
           para-quinone methides
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Venkatram R. Reddy, Narsimulu Maripally, Raghupathi Mutyala, Jagadeesh Babu Nanubolu, Rajesh Chandra
      The hitherto unknown, organocatalysed (DMAP) vinylogous Rauhut-Currier reaction of 2,3-butadienoates with para-quinone methides has been achieved. The products, diarylmethane substituted allenoates, are formed in high to excellent yields under mild reaction conditions.
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      PubDate: 2018-06-11T08:18:36Z
       
  • Enantioselective organocatalytic approach to δ-lactones bearing a
           fused cyclohexanone scaffold
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Dorota Kowalczyk, Łukasz Albrecht
      A new method based on the cascade reaction between β,γ-unsaturated-α-ketophosphonates and cyclic 1,3-dicarbonyls is reported for the synthesis of highly enantiomerically enriched δ-lactones bearing a fused cyclohexenone scaffold. The target products bearing a δ-lactone moiety and one stereogenic center were obtained in good to excellent yields (83–96%) and enantioselectivities (63:32–95:5 er). The best results were obtained in the presence of a chiral Brønsted base catalyst derived from the cinchona alkaloid quinine and modified by a squaramide moiety.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Ferric nitrate-promoted oxidative esterification of toluene with
           N-hydroxyphthalimide: Synthesis of N-hydroxyimide esters
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Pingping Li, Jian Sun, Xiaohe Xu, Zhisheng Mi, Yuyan Lin, Jingya Cheng, Renren Bai, Yuanyuan Xie
      A ferric nitrate-promoted cross-dehydrogenative coupling reaction of N-hydroxyphthalimide (NHPI) with toluene derivatives is reported. The reaction proceeded smoothly using molecular oxygen as an oxidant, providing an efficient method for the synthesis of N-hydroxyimide esters. Furthermore, a plausible mechanism was proposed.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • A direct route for the preparation of Fmoc/OtBu protected iodotyrosine
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Andrew M. Steer, Hannah L. Bolt, William D.G. Brittain, Steven L. Cobb
      Herein the synthesis of an Fmoc/O t Bu orthogonally protected iodotyrosine derivative is reported. This has been achieved via a simple two-step process in an overall 58% yield from commercially available Fmoc-Tyr( t Bu)-OH. The Fmoc/O t Bu orthogonally protected iodotyrosine was also shown to be amenable to Suzuki-Miyaura cross-coupling to deliver a novel bi-aryl tyrosine derivative.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Induced secondary metabolites from the endophytic fungus Aspergillus
           versicolor through bacterial co-culture and OSMAC approaches
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Miada F. Abdelwahab, Tibor Kurtán, Attila Mándi, Werner E.G. Müller, Mostafa A. Fouad, Mohamed S. Kamel, Zhen Liu, Weaam Ebrahim, Georgios Daletos, Peter Proksch
      Two new cryptic 3,4-dihydronaphthalen-(2H)-1-one (1-tetralone) derivatives, aspvanicin A (1) and its epimer aspvanicin B (2), as well as several known cryptic metabolites (3–8), were obtained from the ethyl acetate extract of the co-culture of the endophytic fungus Aspergillus versicolor KU258497 with the bacterium Bacillus subtilis 168 trpC2 on solid rice medium. When A. versicolor was cultured axenically in liquid Wickerham medium supplemented with 3.5% DMSO, an additional three known secondary metabolites (9–11) were isolated that were lacking when the fungus was fermented on rice medium. The structures of the new compounds were elucidated using one- and two-dimensional NMR spectroscopy as well as HRESIMS. The relative and absolute configurations of 1 and 2 were determined by the combination of NMR and electronic circular dichroism (ECD) analysis aided by DFT conformational analysis and TDDFT-ECD calculations. The ECD calculations revealed that although the sign of the blue-shifted overlapping n-π∗ ECD transition follows the helicity rule of cyclic aryl ketones, the calculation of low-energy conformers and ECD spectra was necessary to determine the stereochemistry. All metabolites were assessed for their antibacterial and cytotoxic activities; one of the new diastereomers, compound 2, showed moderate cytotoxic activity against the mouse lymphoma cell line L5178Y.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Pd-catalyzed C-N coupling of primary (het)arylamines with 5-substituted
           3-chloro-4H-1,2,6-thiadiazin-4-ones
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Andreas S. Kalogirou, Panayiotis A. Koutentis
      The Buchwald-Hartwig Pd-catalyzed C-N coupling reaction of 5-substituted 3-chloro-4H-1,2,6-thiadiazin-4-ones with primary (het)arylamines is described, affording twenty new 3,5-disubstituted 4H-1,2,6-thiadiazin-4-ones in 56–99% yield. The protocol enables the mild preparation of difficult to access 3,5-dianilino-1,2,6-4H-thiadiazin-4-ones. The reaction scope and limitations are discussed.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Iron(III) nitrate-induced aerobic and catalytic oxidative cleavage of
           olefins
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Toru Amaya, Hayato Fujimoto
      Microwave-assisted catalytic oxidative cleavage of olefins using Fe(NO3)3·9H2O under O2 is reported. This reaction system is particularly effective when 9-benzylidene-9H-fluorene derivatives are used as substrates even though they are tri- and tetra-substituted olefins.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Epoxidation of vinyl cyanides by calcium hypochlorite under catalyst- and
           solvent-free conditions
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): F. Mirhashemi, M.A. Amrollahi
      In this paper, epoxidation of a wide range of alkenes by calcium hypochlorite (Ca(OCl)2) was investigated under catalyst- and solvent-free conditions. It was noticed that the highest yield was achieved with crushing, when the reaction was between vinyl cyanides and Ca(OCl)2. The structure of the synthesized epoxides was confirmed by IR, 1H and 13C NMR and elemental analysis. Short reaction times, the use of a simple experimental procedure, and reducing of energy consumption are other important advantages of our work that could be mentioned too.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Amine over-alkylation side products in the synthesis of BMS-955176
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Sloan Ayers, Zhongmin Xu, Matthew Haley, Alice Yang, Regina Black, Susanne Kiau
      Over-alkylation side products are common in the alkylation of amines by substitution. In the synthesis of the novel HIV Maturation inhibitor BMS-955176, two over-alkylation byproducts were routinely observed at the penultimate synthetic step, in which a thiomorpholine dioxide side chain was added to the core molecule by alkylation of a primary amine. These two byproducts had drastically different HPLC relative retention times, despite both containing only one additional side chain. Adding complexity to the challenge of solving their structures was the proclivity of the two byproducts to interconvert. Positive- and negative-ion HRMS, as well as isolation and 1D and 2D NMR were utilized to determine their structures. These byproducts were additionally problematic in that they led to daughter impurities at the API step.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Humulene derivatives from Saharian Asteriscus graveolens
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Leila Hammoud, Francisco León, Ignacio Brouard, Javier Gonzalez-Platas, Samir Benayache, Paul Mosset, Fadila Benayache
      Three new sesquiterpene-humulenes, (−)- asteriscunolides I (1), J (2) and (−)-(2Z,6E,9Z)-8-oxo-1α-acetoxy-2,6,9-humulatrien-12-oic acid (3) were isolated from the leaves-flowers of the Saharan medicinal plant Asteriscus graveolens along with six known compounds. The structures of the compounds were determined on the basis of spectroscopic mono and bidimensional NMR, mass spectrometry and by single-crystal X-ray diffraction. Compounds 1–3 were evaluated for cytotoxic assay, no significant activity was detected.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Boranil dyes bearing tetraphenylethene: Synthesis, AIE/AIEE effect
           properties, pH sensitive properties and application in live cell imaging
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Shengxin Chen, Rongmao Qiu, Qiuhan Yu, Xueyan zhang, Ming Wei, Zhenya Dai
      A serial of novel fluorescent boranil dyes (7, 8, 9, 10) bearing tetraphenylethene were prepared through an efficient process. These dyes exhibited large stokes shifts (more than 5000 cm−1) and moderate fluorescent quantum yield from 0.22–0.53. Dye 9 exhibited AIE/AIEE and exhibited weak fluorescence in pure MeCN or the MeCN/water mixture with a water fraction below 80%, in which a significant AIEE effect was observed in the mixture with 80% of water fraction and a sharp increasement in fluorescence intensity was also observed. And dye 8 and 10 showed moderate solvatochromism with the solvent changed from toluene to DMSO, and they displayed sensitivities to pH change in MeCN/water solution. Interestingly, dyes 8 and 10 obtained by column chromatography and slow solvent evaporation showed different X-ray diffraction properties. Moreover, compound 8 and 10 could be applied to cell imaging.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Fusopoltide A and fusosterede A, A polyketide with a pentaleno[1,2-c]pyran
           ring system and A degraded steride, from the fungus Fusarium solani
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Keliang Chen, Weiguang Sun, Qiong Bie, Xiulan Liu, Chunmei Chen, Junjun Liu, Yongbo Xue, Jianping Wang, Zengwei Luo, Hucheng Zhu, Yonghui Zhang
      Fusopoltide A (1), a novel polyketide featured a pentaleno[1,2-c]pyran ring, and fusosteride A (2), a new steride with A/B-ring degraded, together with a known ergosterol peroxide (3), were isolated from a solid culture extract of Fusarium solani. The structures of 1 and 2 were elucidated by detailed interpretation of their HRESIMS and NMR spectroscopic data and their absolute configurations were determined by X-ray crystallographic analysis and the electronic circular dichroic (ECD) method, respectively. The postulated biogenetic pathways of 1 and 2 were also discussed. Compound 1 exhibits inhibitory activity against cyclooxygenase-2 (COX-2) with an IC50 value of 3.45 μM.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Design, synthesis and evaluation of a novel fluorescent probe to
           accurately detect H2S in lysosomes
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Lujuan Liao, Zhenjie Li, Wei Hu, Yan Huang, Bu-min Liu, Lisheng Wang, Mian Wang, Jianyi Wang
      A novel H2S-responsive fluorescent probe Rh-Lyso-H2S has been designed and synthesized. The Rh-Lyso-H2S shows high sensitivity and selectivity toward H2S, with a limit of detection of 3.36 × 10−7 M. The reason is that Rh-Lyso-H2S changed from a stable non-conjugated closed-ring lactone conformation with weak fluorescence to a conjugated open-ring conformation with strong fluorescence in the presence of H2S. The Rh-Lyso-H2S has a good lysosome-targeting capacity and is used to detect lysosomal H2S in living cells, which is driven via the protonation of its basic morpholine moiety by acidic lysosomes. Rh-Lyso-H2S is triggered by H2S via removing the thiophenecarboxylate group, and the corresponding activated mechanism of Rh-Lyso-H2S toward H2S is proposed.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • One pot, three component 1,3 dipolar cycloaddition: Regio and
           diastereoselective synthesis of spiropyrrolidinyl indenoquinoxaline
           derivatives
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Priyabrata Pattanaik, Sabita Nayak, Deepak Ranjan Mishra, Pravati Panda, Bishnu Prasad Raiguru, Nilima Priyadarsini Mishra, Seetaram Mohapatra, N. Arjunreddy Mallampudi, Chandra Shekhar Purohit
      A competent and highly discriminating one-pot synthesis of highly diversified novel functionalized indenoquinoxalone grafted spiropyrrolidine linked chromene-3-carbonitrile conjugates accumulating three pharmocophoric cores, heterocyclic indenoquinoxalone, pyrrolidines and chromene-3-carbonitrile in a single molecular framework by means of 1,3-dipolar cycloaddition reaction between indenoquinoxalone, proline/benzyl amine and chromene-3-carbonitrile in ethanol under classical and microwave conditions is described. The three component 1,3-dipolar cycloaddition reaction proceeds via in situ generation of azomethine ylides by the decarboxylative condensation of indenoquinoxalone with proline/benzyl amine and their selectivity towards the endo cyclic double bonds of dipolarophile (chromene-3-carbonitrile) leading to the formation of highly functionalised regio- and diastereoselective molecular hybrids. This methodology exemplifies the green chemistry protocol such as mild reaction conditions, high yields, one-pot procedure and operational simplicity.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • The enhancement of luminescent properties of Tb3+ complexes with
           tetra-1,3-diketone ligands promoted by the tetrathiacalix[4]arene scaffold
           
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Sergey N. Podyachev, Svetlana N. Sudakova, Gulnaz Sh. Gimazetdinova, Rinas N. Nagimov, Aidar T. Gubaidullin, Victor V. Syakaev, Dmitry V. Lapaev, Olga B. Bazanova
      This is the first report on the synthesis and characterization of tetra-1,3-diketone derivatives of tetrthia- and calix[4]arenes substituted by acetylacetonyl or dipivaloylmethanyl moieties at the upper rim and bearing hydroxyl groups at the lower rim as ligands for Tb3+ complexes. The spatial structure and tautomeric content for the synthesized ligands have been determined by means of X-ray, IR and NMR spectroscopy. Comparison of the sensitizing properties of tetrathiacalix[4]arenes and their calix[4]arene analogues on the Tb3+-centered luminescence in DMF solutions has been performed. A substantial enhancement of the luminescent properties of Tb3+- complexes with tetra-1,3-diketone ligands promoted by the tetrathiacalix[4]arene scaffold was established.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Merging photoredox catalysis with allylboration. The photochemical
           perfluoroalkylation of unsaturated potassium alkyltrifluoroborates and
           synthesis of fluorinated alcohols
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Marcin Kublicki, Krzysztof Durka, Tomasz Kliś
      The development of a visible light-mediated atom transfer radical addition (ATRA) of perfluoroalkyl iodides to potassium 1-penten-5-yl-, vinyl- and allyltrifluoroborates using the reductive quenching of [Ru(bpy)3]Cl2 or [Ru(bpy)3](PF6)2 is described. Using an operationally simple and mild protocol, the corresponding potassium trifluoroborates containing perfluoroalkyl groups were obtained in moderate to high yields. In the case of potassium allyltrifluoroborate, the use of acetone as the solvent resulted in allylboration followed by ATRA of perfluoroalkyl iodides to the formed homoallyl alcohol. A one-pot protocol was developed for the synthesis of a series of fluorinated alcohols using potassium allyltrifluoroborate, perfluoroalkyl iodides and selected aliphatic ketones.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Highly efficient organic photosensitizer with aggregation-induced emission
           for imaging-guided photodynamic ablation of cancer cells
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Yipeng Li, Qi Yu, Pengli Gao, Huiran Yang, Tianci Huang, Shujuan Liu, Qiang Zhao
      We design an organic photosensitizer with a donor-π-acceptor configuration. The photosensitizer exhibits aggregation-induced emission characteristics and efficient singlet oxygen production in the aggregated state. It is then enveloped into the water-soluble micelle to afford a nanoprobe. The water-soluble nanoprobe keeps the photosensitizer in the aggregation state and is used for imaging-guided photodynamic ablation of cancer cells.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Total synthesis of Carpatamides A–D
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Nagaraju Madala, Venkata Rao Ghanta, Srilalitha Vinnakota, Narender Mendu, Arun B. Ingle, Krishna Ethiraj, Vishal Sharma
      A synthetic strategy was developed for the synthesis of the common core structure of Carpatamides A–D. The total synthesis of Carpatamides A and C was completed in 6 steps and of Carpatamides B and D in 7 steps, by employing the Wittig olefination, olefin cross metathesis and acid amine coupling reactions as key steps.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
  • Diverted total synthesis of melodorinol analogues and evaluation of their
           cytotoxicity
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27
      Author(s): Tanatorn Khotavivattana, Thitiphong Khamkhenshorngphanuch, Kitiya Rassamee, Pongpun Siripong, Tirayut Vilaivan
      A series of melodorinol analogues were synthesized via a diverted total synthesis approach, leading to structural modifications on several regions of the molecule. Their cytotoxicity was evaluated against five human cancer cell lines (KB, HeLa-S3, MCF-7, HT-29 and A549). Structure-activity relationship studies revealed key parameters that affect the cytotoxicity. In particular, the novel 4-bromo-furanone analogues exhibited greater cytotoxicity compared to the corresponding non-brominated analogues. The stereochemistry at C-6 and the nature of acyl substituents on the C-6 and C-7 hydroxyl groups also play an important role. The most potent analogues exhibit approximately 15-fold higher cytotoxicity towards KB and HeLa-S3 than melodorinol and also show exceptionally high potency against MCF-7, HT-29 and A549 cell lines.
      Graphical abstract image

      PubDate: 2018-06-11T08:18:36Z
       
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    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27


      PubDate: 2018-06-11T08:18:36Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27


      PubDate: 2018-06-11T08:18:36Z
       
  • Graphical abstract TOC
    • Abstract: Publication date: 4 July 2018
      Source:Tetrahedron Letters, Volume 59, Issue 27


      PubDate: 2018-06-11T08:18:36Z
       
 
 
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