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
基金：
英国医学研究理事会;
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
收藏
页码：49 / 53
页数：5
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