PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS USING ENZYMES .3. ENZYMATIC PREPARATION OF ENANTIOMERICALLY ENRICHED TERTIARY ALPHA-BENZYLOXY ACID-ESTERS - APPLICATION TO THE SYNTHESIS OF (S)-(-)-FRONTALIN

被引：59

作者：

SUGAI, T ^{[1
]}

KAKEYA, H ^{[1
]}

OHTA, H ^{[1
]}

机构：

[1] KEIO UNIV,FAC SCI & TECHNOL,DEPT CHEM,HIYOSHI 3-14-1,KOHOKU KU,YOKOHAMA,KANAGAWA 223,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 15期

关键词：

D O I：

10.1021/jo00302a031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enzymatic preparation of enantiomerically enriched tertiary a-benzyloxy acid esters is described. Enantioselective hydrolysis of the racemic esters of the formula [R-C(CH3)(OCH2Ph)CO2CH3] by lipase OF (from Candida cylindracea, Meito Sangyo Co.) was successfully carried out on a preparative scale. With the asymmetric carbon atom possessing a tertiary benzyloxy group, (S)-(-)-frontalin, a component of the aggregation pheromone of the southern pine beetle, was efficiently synthesized. © 1990, American Chemical Society. All rights reserved.

引用

页码：4643 / 4647

页数：5

共 23 条

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