An easy and versatile approach to the synthesis of chiral pheromone lactones via 4,4-dimethyl-2-oxazoline derivatives

As part of our ongoing investigation on the versatility of 4,4-dimethyl-2-oxazoline derivatives, we present a straightforward synthesis of chiral lactone pheromones from readily available starting materials. As an application, we describe the diastereoselective synthesis of cis and trans-2-methyl-5-hexanolide (1), a pheromone component of the carpenter bee Xylocopa hirutissima, and a formal synthesis of (4R,5Z)-5-tetradecen-4-olide (2), the sex pheromone of the Japanese beetle Popillia japonica.