Enantioselective synthesis of Anomala osakana pheromone and Janus integer pheromone: a flexible approach to chiral γ-butyrolactones

Abstract

The enantioselective synthesis of Anomala osakana pheromone and Janus integer pheromone has been achieved without using any protecting groups. The synthesis involved using an asymmetric alkynylation to obtain gamma-hydroxy-alpha,beta-acetylenic esters with high ee (84%) and yields ( approximately 80%), followed by selective hydrogenation and lactonization in high overall yields (87% and 89%).