Synthesis of (±)-methyl tetradeca-trans-2,4,5-trienoate, the allenic sex pheremone produced by the male dried bean beetle

Abstract

Dodeca-2,3-dien-1-ol was synthesised by the reductive elimination of the tetrahydropyran-2′-yloxy group from 4-tetrahydropyran-2′-yloxydodec-2-yn-1-ol, and oxidised with active manganese dioxide to the corresponding allenic aldehyde which, on treatment with the anion of trimethyl phosphonoacetate, gave (±)-methyl tetradeca-trans-2,4,5-trienoate.