Concise organocatalyzed epoxidation based total synthesis of (−)- and (+)-trans-posticlures and (−)-(6Z,9Z,4S,5S)-trans-4,5-epoxynonadeca-6,9-diene

Abstract

A concise, flexible and efficient organocatalytic strategy has been developed for the enantioselective synthesis of (−)-trans- and (+)-trans-posticlures, along with (−)-(6Z,9Z,4S,5S)-trans-4,5-epoxynonadeca-6,9-diene which are remarkable natural trans-epoxide pheromones. The key transformations in this approach involve an organocatalyzed asymmetric Jørgensen epoxidation and stereoselective (Z)-Wittig olefination. Notably, the Jørgensen epoxidation step ensures excellent enantiopurity (up to 97% ee) in the synthesis of the target pheromone antipodes.