Stereoselective Synthesis of (5R, 65)-(-) Erythro-6-Acetoxy-5-Dodecanolide, A Lower Homologue of a Mosquito Oviposition Attractant Pheromone, from Argentilactone

Abstract

Starting from argentilactone [(5R)-(-)- δ -lactone of 5-hydroxydodeca-Z,Z-2,6-dienoic acid] and via the hydrobromic acid opening of the 65, 75-epoxide followed by acetylation and catalytic hydrogenation of the corresponding bromohydrin, (5R, 65)-(-)-erythro-6-acetoxy-5-dodecanolide was obtained. Through the 6R, 7R-epoxide and following the same sequence, the stereoisomer (5R, 6R)-(+)-threo-6-acetoxy-5-dodecanolide, was also synthesized.