ASYMMETRIC-SYNTHESIS OF (-)-(1R,2S)-CISPENTACIN AND RELATED CIS-2-AMINO AND TRANS-2-AMINO CYCLOPENTANE-1-CARBOXYLIC AND CYCLOHEXANE-1-CARBOXYLIC ACIDS

被引:90
作者
DAVIES, SG
ICHIHARA, O
LENOIR, I
WALTERS, IAS
机构
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 11期
关键词
D O I
10.1039/p19940001411
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The antifungal antibiotic (-)-(1R,2S)-2-aminocyclopentane-1-carboxylic acid (cispentacin) 8 and its cyclohexane homologue 14 have been prepared utilizing the highly stereoselective conjugate addition of homochiral lithium N-benzyl-N-alpha-methylbenzylamide 5. The corresponding trans-beta-amino acids 10 and 16 were also prepared via the selective epimerization of the cis-beta-amino ester conjugate addition products.
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页码:1411 / 1415
页数:5
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