Enantioselective Synthesis of Macrolide Pheromones, (5Z, 13S)-5-Tetradecen-13-olide and (9R)-Decan-9-olide, by Using Mn-Salen Catalyzed Asymmetric Epoxidation as a Key Step

Abstract

Highly enantioselective epoxidation of cis-enynes catalyzed by the newly developed Mn-salen catalyst 1 and subsequent LAH reduction provided optically active homopropargylic alcohols which served as useful building blocks for the synthesis of various pheromones. For example, (5Z, 13S)-5-tetradecen-13-olide and (9R)-decan-9-olide were synthesized from cis-enynes in a straightforward manner by using asymmetric epoxidation as a key step.