Facile synthesis of (Z)-tetracos-5-enoic acid and racemic cis-4-(2-octadecylcyclopropane-1-yl)-butanoic acid

被引：6

作者：

Coxon, GD

Douglas, JD

Minnikin, DE ^{[1
]}

机构：

[1] Univ Birmingham, Sch Biosci, Birmingham B15 2TT, W Midlands, England

[2] Univ Newcastle Upon Tyne, Dept Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 2003年 / 126卷 / 01期

关键词：

fatty acids; mycolic acids; cyclopropane rings; Wittig reaction; alkene stereochemistry;

D O I：

10.1016/S0009-3084(03)00092-6

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

(Z)-Tetracos-5-enoic acid and racemic cis-4-(2-octadecylcyclopropane-1-yl)-butanoic acid have been prepared from 1-eicosene by a new facile route. Periodic acid cleavage of the epoxide of 1-eicosene gave nonadecanal which was condensed with 4-carboxybutyltriphenylphosphonium bromide to give predominately (Z)-tetracos-5-enoic acid. Simmons-Smith type cyclopropanation of (Z)-tetracos-5-enoic acid gave a minor proportion of racemic cis-4-(2-octadecyleyclopropane-1-yl)-butanoic acid accompanied by major amounts of its methyl ester. (C) 2003 Elsevier Ireland Ltd. All rights reserved.

引用

页码：49 / 53

页数：5

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