Abstract
Abstract A kinetic resolution of methyl 4-hydroxy-5-tetradecynoate is accomplished by a lipase-catalyzed enantioselective acylation in organic solvent. Acylation of methyl 4-hydroxy-5-tetradecynoate with succinic anhydride in an organic solvent yields methyl (R)-4-succinoyloxy-5-tetradecynoate with over 90% e.e.. Furthermore, this optically active diester was converted to (R)-5-(1-decynyl)oxacyclopentan-2-one by lipase-catalyzed enantioselective lactonization which enhanced its e.e. over 99%. The Japanese beetle pheromone (R,Z)-(-)-5-(1-decenyl)oxacyclopentan-2-one is synthesized in one step from this optically active lactone.
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