Stereoselective synthesis of (6Z, 10E, 12Z)-octadeca-6, 10, 12-trienoic acid,(8Z, 12E, 14Z)-eicosa-8, 12, 14-trienoic acid, and their [1-14 C]-radiolabeled analogs

O Loreau, JM Chardigny, JL Sebedio…

Index: Loreau; Chardigny; Sebedio; Noel Chemistry and Physics of Lipids, 2003 , vol. 124, # 2 p. 135 - 145

Full Text: HTML

Citation Number: 1

Abstract

To study the metabolic fate of conjugated linoleic acid isomers, we synthesized, in seven steps, from 1-heptyne,(6Z, 10E, 12Z)-octadeca-6, 10, 12-trienoic acid,(8Z, 12E, 14Z)-eicosa- 8, 12, 14-trienoic acid, and their [1-14C]-analogs. In the case of (6Z, 10E, 12Z)- octadecatrienoic acid, a series of palladium-catalyzed cross-coupling reactions between 1- heptyne and (E)-1, 2-dichloro-ethene, a coupling reaction with a Grignard reagent and ...