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

2004; Elsevier BV; Volume: 45; Issue: 40 Linguagem: Inglês

10.1016/j.tetlet.2004.08.083

1873-3581

Paulo H. G. Zarbin, Alfredo R. M. Oliveira, Fábio Simonelli, José Augusto Ferreira Perez Villar, Orlando Jr. Delay,

Synthetic Organic Chemistry Methods

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.