A Versatile Approach Towards Enantiopure α-Methyl β-Hydroxy Ketones. Application to the Synthesis of (4R,5S) Sitophilure and of Its Stereoisomers

Abstract

Rice weevil pheromone sitophilure ((4R,5S)-5-hydroxy-4-methyl-3-heptanone) and its three diastereomers were synthesized in three steps, starting from 3-(trimethylsilyloxy)-1,3-pentadiene and propionaldehyde. Other optically active α-methyl β-hydroxy ketones can also be synthesized by the reported procedure.