Stereoselective synthesis of unsaturated very long chain fatty acid methyl esters

Article abstract of DOI:10.1016/S0040-4039(99)00666-8

Very long chain fatty acids are isolated from many different natural sources. However their unsaturated and particularly their diunsaturated derivatives with a Δ(n,n+4) pattern are almost exclusively encountered in marine organisms, until we found some derivatives in the botanical family of the Annonaceae. In this letter we present a very efficient synthesis of this family of products based on the new transition metal-catalyzed coupling reaction between an organomagnesium reagent and a functionalized vinyl bromide.