A general synthetic route towards γ- and δ-lactones. Total asymmetric synthesis of (-)-muricatacin and the mosquito oviposition pheromone (5R, 6s)- 6-acetoxy-hexadecanolide

Article abstract of DOI:10.1016/S0040-4039(99)00895-3

Five (or six) membered asymmetric lactones are synthesized from γ- butyrolactone (or δ-valerolactone) in a straightforward way using the following reaction sequence: reduction, Wittig-Schlosser coupling, Sharpless asymmetric dihydroxylation, oxidation and lactonization. Thus, (-)muricatacin is synthesized in six steps (43% overall yield). Furthermore, (5R,6S)-6- acetoxy-hexadecanolide is prepared in eight steps (38% overall yield) via a carbonate ester, utilizing a novel lactonization with inversion of stereochemistry.