Short-route synthesis of (3E,5Z)-tetradecadienoic acid (megatomic acid), the sex attractant of the black carpet beetle

Abstract

A new and expeditious route to (3E,5Z)-3,5-tetradecadienoic acid (megatomic acid), the sex attractant of the black carpet beetle Attagenus megatoma (Fabricius), is reported which proceeds with 97% stereoselectivity; Cadiot–Chodkiewicz cross-coupling of 1-decyne and 4-bromo-3-butyn-1-ol in the presence of CuCl, followed by stereoselective reductions and Jones oxidation, gives the target molecule, with the synthetic pheromone showing a positive electrophysiological response.