Tetrahedron p. 6223 - 6230 (1991)
Update date:2022-08-10
Topics:
Fukusaki, Eiichiro
Senda, Shuji
Nakazono, Yutaka
Omata, Tetsuo
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.
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(1985)