SYNTHESIS OF METHYL (5Z,8Z,11Z,14Z,17E)-EICOSAPENTAENOATE AND METHYL (4Z,7Z,10Z,13Z,16Z,19E)-DOCOSAHEXAENOATE

被引：23

作者：

VATELE, JM ^{[1
]}

DOAN, HD ^{[1
]}

CHARDIGNY, JM ^{[1
]}

SEBEDIO, JL ^{[1
]}

GRANDGIRARD, A ^{[1
]}

机构：

[1] INRA,UNITE NUTR LIPID,F-21034 DIJON,FRANCE

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 1994年 / 74卷 / 02期

关键词：

WITTIG REACTION; CATALYZED ACETYLENIC COUPLING; BETA; GAMMA-UNSATURATED ALDEHYDES; N-3 TRANS POLYUNSATURATED FATTY ACIDS;

D O I：

10.1016/0009-3084(94)90059-0

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：

(3Z,6Z,9Z,12E)-Pentadecatetraenal, a common intermediate in the synthesis of methyl Delta 17t EPA and methyl Delta 19t DHA, was obtained by copper(I)-catalyzed coupling between the Grignard reagent of 1,1-diethoxy-3-butyne and (Z,E)-1-bromo-5,8-undecadien-2-yne followed by semi-hydrogenation of the resulting diendyne. The tetraenic aldehyde was subjected to a Wittig reaction with the ylide of (3-carboxybutyl)triphenylphosphonium bromide or of [6-(2,6,7-trioxabicyclo [2.2.2] octyl)-hex-3-Z-enyl] triphenylphosphonium iodide to give, respectively Delta 17t EPA and the protected Delta 19t DHA in high isomeric purity.

引用

页码：185 / 193

页数：9

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