Intramolecular S(N)2 ring opening of a cyclic sulfate: Synthesis of erythro-(-)-6-acetoxy-5-hexadecanolide - a major component of mosquito oviposition attractant pheromone

Article abstract of DOI:10.1016/S0957-4166(97)00011-6

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 sulfate 8 is oxidized to the cyclic sulfate 2. Highly regio- and stereospecific ring opening of (4S,5S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield.