Synthesis of 2′,3′-cyclohexen bicyclic uridine analogues using ring-closure metathesis

被引:6
|
作者
Drone, Jullien
Egorov, Maxim
Hatton, Wilfried
Bertrand, Marie-Jo
Len, Christophe
Lebreton, Jacques
机构
[1] Univ Nantes, CNRS, UMR 6513, Synth Organ Lab, F-44322 Nantes 3, France
[2] Univ Poitiers, CNRS, UMR 6514, FR 2703, F-86022 Poitiers, France
关键词
antivirals; nucleic acid analogues; radical allylation; ring-closure metathesis;
D O I
10.1055/s-2006-941568
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of two new 2',3'-cyclohexen bicyclic uridine analogues is described. From 5'-protected uridine two successive tin radical-mediated allylations at 2'-C and 3'-C position followed by ring-closure olefin metathesis on the diene intermediate using Grubbs' catalyst led to the formation of the six-membered ring.
引用
收藏
页码:1339 / 1342
页数:4
相关论文
共 50 条
  • [31] PALLADIUM-CATALYZED DIBENZOFURAN SYNTHESIS BY DEHYDROGENATIVE RING-CLOSURE
    SHIOTANI, A
    ITATANI, H
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (11): : 1236 - 1241
  • [32] Studies towards the synthesis of the bicyclic 3,8-secotaxane diterpenoid system using a ring closing metathesis strategy
    Renzulli, Michela L.
    Rocheblave, Luc
    Avramova, Stanislava I.
    Galletti, Elena
    Castagnolo, Daniele
    Tafi, Andrea
    Corelli, Federico
    Botta, Maurizio
    TETRAHEDRON, 2007, 63 (02) : 497 - 509
  • [33] NEW PURINE RING-CLOSURE AND SYNTHESIS OF 2-SUBSTITUTED DERIVATIVES OF ADENOSINE CYCLIC 3',5'-PHOSPHATE
    MEYER, RB
    SHUMAN, DA
    ROBINS, RK
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (15) : 4962 - 4966
  • [34] Synthesis of novel unsaturated bicyclic lactams by ring-closing metathesis
    Grossmith, CE
    Senia, F
    Wagner, J
    SYNLETT, 1999, (10) : 1660 - 1662
  • [35] Synthesis and Insecticidal Evaluation of Neonicotinoid Analogues with Bicyclic Ring System
    Chen, Yinbo
    Fan, Jie
    Xia, Shuang
    Cheng, Jiagao
    Xu, Xiaoyong
    Li, Zhong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (02) : 409 - 413
  • [36] Efficient highly stereoselective synthesis of olefinic macrocyclic crown-formazans with the Z-configuration via ring-closure metathesis
    Ibrahim, YA
    Behbehani, H
    Ibrahim, MR
    Abrar, NM
    TETRAHEDRON LETTERS, 2002, 43 (39) : 6971 - 6974
  • [37] Synthesis of 5-/10-membered ring analogues of the dienediyne core of neocarzinostatine chromophore by palladium(0)-mediated ring-closure reaction
    Suffert, J
    Abraham, E
    Raeppel, S
    Bruckner, R
    LIEBIGS ANNALEN, 1996, (04): : 447 - 456
  • [38] SIMULATED ANNEALING OF RINGS USING AN EXACT RING-CLOSURE ALGORITHM
    GUARNIERI, F
    WILSON, SR
    TETRAHEDRON, 1992, 48 (21) : 4271 - 4282
  • [39] Application of olefin metathesis to the synthesis of ABE ring analogues of methyllycaconitine
    Barker, D
    McLeod, MD
    Brimble, MA
    Savage, GP
    TETRAHEDRON LETTERS, 2002, 43 (34) : 6019 - 6022
  • [40] Towards taxane analogues synthesis by dienyne ring closing metathesis
    Perez-Estrada, S.
    Sayar, N.
    Granja, J. R.
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (10): : 1331 - 1336