Facile stereoselective synthesis of gamma-substituted gamma-amino acids from the corresponding alpha-amino acids

被引:69
作者
Smrcina, M
Majer, P
Majerova, E
Guerassina, TA
Eissenstat, MA
机构
[1] Structural Biochemistry Program, National Cancer Institute, Frederick Cancer R. and D. Center, Frederick
关键词
D O I
10.1016/S0040-4020(97)00840-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile stereoselective method for the synthesis of gamma-substituted, gamma-amino acids from alpha-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of alpha-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's acid undergoes thermal decarboxylative ring closure to a 5-substituted pyrrolidinone which yields, the corresponding gamma-amino acid after basic hydrolysis. The overall yield of the procedure ranges from 40 to 65%. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:12867 / 12874
页数:8
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