A General Approach to the Synthesis of Butanolides: Synthesis of the Sex Pheromone of the Japanese Beetle

Article abstract of DOI:10.1021/jo00290a018

A variety of substituted γ-hydroxy olefins 1 have been converted to butanolides 4 in very high yield in a three-step sequence involving bromoetherification, elimination, and oxidative cleavage.The key step in the overall transformation is the highly selective oxidative cleavage of enol ethers 3 with PCC under very mild reaction conditions.Application of this methodology has been exemplified in the synthesis of the Japanese beetle pheromone.