PRACTICAL, ASYMMETRIC-SYNTHESIS OF THE CYCLOHEXYL C-28-C-34 FRAGMENT OF THE IMMUNOSUPPRESSANT FK-506 VIA (S)-(-)-3-CYCLOHEXENECARBOXYLIC ACID

被引：10

作者：

CHINI, M

CROTTI, P

MACCHIA, F

PINESCHI, M

FLIPPIN, LA

机构：

[1] UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56126 PISA,ITALY

[2] SAN FRANCISCO STATE UNIV,DEPT CHEM & BIOCHEM,SAN FRANCISCO,CA 94132

来源：

TETRAHEDRON | 1992年 / 48卷 / 03期

关键词：

D O I：

10.1016/S0040-4020(01)89015-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of the cyclohexyl fragment of FK-506 is reported. This new synthesis (five steps, 30% overall yield) starts, for the first time, from (S)-(-)-3-cyclohexenecarboxylic acid (S-2) instead of the commonly used R form (acid R-2) and utilizes an epimerization reaction. The overall yield is improved to 35% by recycling recovered starting product (hydroxy ester 7c) from the epimerization step.

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页码：539 / 544

页数：6

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