Intramolecular S N2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone

Abstract

Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-α followed by treatment with thionyl chloride to furnish cyclic sulfite 8 as the major product. The cyclic sulfite 8 is oxidized to the cyclic sulfate 2. Highly regio- and stereospecific ring opening of (4 S,5 S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5 R,6 S)-6-hydroxy-5-hexadecanolide, 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield.