(7Z,11Z)-Hexadecadienyl acetate (Z7Z11-16:OAc) (1) and its geometric isomer (7Z,11E)-hexadecadienyl acetate (Z7E11-16:OAc) (2) have been conclusively identified as the sex pheromone of Pectinophora gossypiella (Lepidoptera: Gelechiidae). Pheromone-based mass trapping and mating disruption have significantly reduced P gossypiella populations across global cotton production areas. Synthesis of these two active components from commercially available starting materials, 2-(3-bromopropyl)-1,3-dioxolane, DHP, and 7-bromoheptyl acetate, is reported. The pivotal step involves constructing a cis double bond via the Wittig reaction and preparing a trans enol through DHP (3,4-2H-dihydropyran) ring opening. Our results provide a facile and efficient way to obtain active insect pheromones.
Wang et al. (Sat,) studied this question.