Rapid access to acyclic nucleosides via conjugate addition

被引:36
|
作者
Guillarme, S
Legoupy, S
Aubertin, AM
Olicard, C
Bourgougnon, N
Hueta, F
机构
[1] Univ Maine, Fac Sci & Tech, UMR CNRS 6011, Organ Synth Lab, F-72085 Le Mans 9, France
[2] Univ Strasbourg, INSERM U544, Fac Med, Inst Virol, F-67000 Strasbourg, France
[3] Ctr Rech & Enseignement Yves Coppens, Lab Biol & Chim Mol, F-56017 Vannes, France
关键词
Michael addition; acyclic nucleosides; deaza purine and deaza pyrimidine; analogs of penciclovir;
D O I
10.1016/S0040-4020(03)00190-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of several acyclic nucleosides 5 and 6, analogs of penciclovir, was achieved by Michael addition as the key step. This reaction worked not only for the protected natural bases but even for the less nucleophilic deaza purine and deaza pyrimidine. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2177 / 2184
页数:8
相关论文
共 50 条
  • [1] Synthesis of Chiral Acyclic Pyrimidine Nucleosides with a Sulfur-Containing Side Chain via Enantioselective Tandem Conjugate Addition/Protonation
    Li, Jian-Ping
    Tuo, Hao-Ran
    Xie, Ming-Sheng
    Kang, Bo
    Qu, Gui-Rong
    Guo, Hai-Ming
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (01) : 128 - 132
  • [2] Asymmetric conjugate addition of alkylzirconium reagents to α,β-unsaturated thioesters: access to fragrances and acyclic stereochemical arrays
    Gao, Zhenbo
    Fletcher, Stephen P.
    CHEMICAL COMMUNICATIONS, 2017, 53 (73) : 10216 - 10219
  • [3] An Efficient Protocol for the Synthesis of Carboacyclic Nucleosides via Aza-Conjugate Addition Reaction
    Zolfigol, Mohammad Ali
    Khazaei, Ardeshir
    Moosavi-Zare, Ahmad Reza
    Zare, Abdolkarim
    Hasanijejad, Ali Reza
    IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION, 2010, 29 (04): : 67 - 73
  • [4] Access to 2-alkyl chromanones via a conjugate addition approach
    Stubbing, Louise A.
    Li, Freda F.
    Furkert, Daniel P.
    Caprio, Vittorio E.
    Brimble, Margaret A.
    TETRAHEDRON, 2012, 68 (34) : 6948 - 6956
  • [5] Microwave-promoted Michael addition in neat water: A rapid, efficient and green method for the preparation of acyclic nucleosides
    Qu, Gui-Rong
    Zhang, Zhi-Guang
    Geng, Ming-Wei
    Xia, Ran
    Zhao, Lin
    Guo, Hai-Ming
    SYNLETT, 2007, (05) : 721 - 724
  • [6] Synthesis of 4'-C-methylcarbocyclic nucleosides via conjugate addition of D-4-methylcyclopentenone
    Liu, Peng
    Schinazi, Raymond F.
    Chu, C. K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [7] Intramolecular conjugate addition of γ- and δ-trichloroacetimidoyloxy-α,β-unsaturated esters in an acyclic system
    Matsushima, Yoshitaka
    Kino, Jun
    TETRAHEDRON, 2008, 64 (18) : 3943 - 3952
  • [8] Diastereoselectivity and mechanism of conjugate addition of organocuprates to γ-chiral acyclic enones and enoates
    Yamamoto, K
    Yamada, S
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1999, 57 (09) : 763 - 774
  • [9] Highly enantioselective organocatalytic conjugate addition of malonates to acyclic α,β-unsaturated enones
    Halland, N
    Aburel, PS
    Jorgensen, KA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (06) : 661 - 665
  • [10] Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir
    Qin, Tao
    Li, Jian-Ping
    Xie, Ming-Sheng
    Qu, Gui-Rong
    Guo, Hai-Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (24): : 15512 - 15523