Syntheses of three metabolites of icosapentaenoic and docosahexaenoic acids

Abstract

Starting from the n − 3 polyunsaturated fatty acids icosapentaenoic acid (1, EPA) and docosahexaenoic acid (2, DHA), the syntheses of methyl 2E,4Z,8Z,11Z,14Z,17Z-icosa-2,4,8,11,14,17-hexaenoate (6), 2E,8Z,11Z,14Z,17Z-icosa-2,8,11,14,17-pentaenoate (7) and 2E,4Z,7Z,10Z,13Z,16Z,19Z-docosa-2,4,7,10,13,16,19-heptaenoate (8), in high stereochemical purity, have been accomplished. The corresponding carboxylic acids have been reported as metabolites in the bioconversion of EPA and DHA.