Preparation of methylcis-9,cis-12,cis-15-octadecatrienoate-15,16-d2 and methylcis-9,cis-12,cis-15-octadecatrienoate-6,6,7,7-d4

Methylcis-9,cis-12,cis-15-octadecatrienoate-15,16-d 2 was obtained from Wittig coupling of methyl 12-oxo-cis-9-dodecenoate,18, and 3,4-dideutero-cis-3-hexenyltriphenylphosphonium bromide,16. Compound18 was obtained by periodic acid oxidation of methyl 12,13-dihydroxy-cis-9-octadecenoate,17, obtained fromVernonia oil. Compound18 also was synthesized from methyl oleate as the starting material. The deuterated fragment,16, was prepared from 3-hexynol and using Lindlar's catalyst and deuterium gas to introduce the deuterium atoms.