Asymmetric Synthesis of Three Alkenyl Epoxides: Crafting the Sex Pheromones of the Elm Spanworm and the Painted Apple Moth
A concise synthesis of the sex Gymnema pheromones of elm spanworm as well as painted apple moth has been achieved.The key steps were the alkylation of acetylide ion, Sharpless asymmetric epoxidation and Brown’s P2-Ni reduction.This approach provided the sex pheromone of the elm spanworm (1) in 31% total yield and those of the painted apple moth (