Organocatalyzed epoxidation in the total synthesis of (−)-trans-, (+)-trans- and (+)-cis-disparlures

Abstract

A simple, flexible and efficient organocatalyzed synthetic approach for the synthesis of (−)-trans-, (+)-trans- and (+)-cis-disparlures has been described. The pivotal reaction sequence comprises organocatalyzed asymmetric Jørgensen epoxidation, Wittig olefination, migration of epoxide and Mitsunobu inversion reaction. Excellent enantiomeric purity (≥99%) was achieved during the synthesis of disparlure enantiomers by the Jørgensen epoxidation key step.