Synthesis of all Four Stereoisomers of Leucomalure, Components of the Female Sex Pheromone of the Stain Moth, Leucoma salicis

摘要

Lipase PS-C(Amano)-catalyzed asymmetric acetylation of (+-)-4-(tert-butyldiphenylsilyloxy)-cis-2,3-epoxy-1-butanol afforded the (2R,3S)-epoxy alcohol and the (2S, 3R)-epoxyacetate, which were converted into all of the four stereoisomers of leucomalure [(3Z)-cis-6,7-cis-9,10-diepoxy-3-henicosene], the female sex pheromone of the Satin moth, Leucoma salicis.