EFFICIENT AND PRACTICAL ASYMMETRIC-SYNTHESIS OF THE TAXOL C-13 SIDE-CHAIN, N-BENZOYL-(2R,3S)-3-PHENYLISOSERINE, AND ITS ANALOGS VIA CHIRAL 3-HYDROXY-4-ARYL-BETA-LACTAMS THROUGH CHIRAL ESTER ENOLATE-IMINE CYCLOCONDENSATION

被引:211
作者
OJIMA, I [1 ]
HABUS, I [1 ]
ZHAO, MZ [1 ]
GEORG, GI [1 ]
JAYASINGHE, LR [1 ]
机构
[1] UNIV KANSAS,DEPT MED CHEM,LAWRENCE,KS 66045
关键词
D O I
10.1021/jo00005a003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-beta-lactams with > 96% ee is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogues.
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页码:1681 / 1683
页数:3
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