A novel approach to unsaturated acyclic nucleoside analogues and the first synthesis of d4T by ring closure metathesis

被引：22

作者：

Ewing, D

Glaçon, V

Mackenzie, G

Postel, D

Len, C

机构：

[1] Univ Picardie, Lab Glucides, F-80039 Amiens, France

[2] Univ Hull, Ctr Organ & Biol Chem, Kingston Upon Hull HU6 7RX, N Humberside, England

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 19期

关键词：

unsaturated acyclic nucleosides; ring closure metathesis; d4T;

D O I：

10.1016/S0040-4039(02)00572-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel unsaturated acyclic nucleoside analogues, 1-{1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}uracil. 1-{1-[1- (hydroxymethyl)prop-2-enyloxy]prop-2-enyl}thymine and 1-{1-[1-(hydroxymethyl)prop-2-enyloxy]prop-2-enyl}cytosine have been prepared in good yield from uridine and 5-methyluridine by periodate cleavage followed by a double Wittig reaction which introduces two vinyl groups. The thymine derivative underwent ring closure metathesis to give a novel synthesis of d4T. (C) 2002 Elsevier Science Ltd. All rights reserved.

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收藏

页码：3503 / 3505

页数：3

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