LIPASE-CATALYZED KINETIC RESOLUTION OF METHYL 4-HYDROXY-5-TETRADECYNOATE AND ITS APPLICATION TO A FACILE SYNTHESIS OF JAPANESE BEETLE PHEROMONE

Article abstract of DOI:10.1016/S0040-4020(01)86554-6

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 a organic solvent yields methyl (R)-4-succinoyloxy-5-tetradecynoate with over 90percent e.e..Furthermore, this optically active diester was converted to (R)-5-(1-decynyl)oxacyclopentane-2-one by lipase-catalyzed enantioselective lactonization which enhanced its e.e. over 99percent.The Japanese beetle pheromone (R,Z)-(-)-5-(1-decenyl)oxacyclopentan-2-one is synthesized in one step from this optically active lactone.