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

被引：43

作者：

FUKUSAKI, E

SENDA, S

NAKAZONO, Y

OMATA, T

机构：

[1] Medical and Membrane Research Laboratory, Nitto Denko Co. 1-1-2, Ibaraki, Osaka, 567, Shimohozumi

来源：

TETRAHEDRON | 1991年 / 47卷 / 32期

关键词：

D O I：

10.1016/S0040-4020(01)86554-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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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页码：6223 / 6230

页数：8

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