Chemistry and physics of lipids

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

GD Coxon, JD Douglas, DE Minnikin

Index: Coxon, Geoffrey D.; Douglas, James D.; Minnikin, David E. Chemistry and Physics of Lipids, 2003 , vol. 126, # 1 p. 49 - 53

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Citation Number: 2

Abstract

(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 ...