New synthesis of a stereoisomeric mixture of methyl 12-trishomofarnesoate,a juvenile hormone mimic useful in sericulture by increasing silk production

A mixture of (e,z)-isomers of methyl 12-trishomofarnesoate (methyl 3,7,11- trimethyl-2,6,10-pentadecatrienoate),a juvenile hormone mimic,was synthesized in nine steps (32.6% overall yield) by starting from only four commercially available materials: 2-hexanone,vinylmagnesium bromide,methyl acetoacetate and trimethyl phosphonoacetate. the mimic is useful in increasing the yield of silk by elongating the larval period of the silkworm,bombyx mori (l.). © 2017 the japan academy.