Stereoconvergent synthesis of (2S,3S,8S,9S,4E,6E)-N-Boc-ADDA starting from (S)-serine and (S)-phenyllactic acid

被引:35
作者
DAniello, F
Mann, A
Schoenfelder, A
Taddei, M
机构
[1] CNRS,CTR NEUROCHIM,UPR 421,LAB PHARMACOCHIM MOL,F-67084 STRASBOURG,FRANCE
[2] UNIV SASSARI,DIPARTIMENTO CHIM,I-07100 SASSARI,ITALY
关键词
D O I
10.1016/S0040-4020(96)01056-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The important naturally occurring beta-amino acid N-Boc-ADDA is prepared following a disconnection of the C-C bond between the two E,E double bonds. The stereochemistry of the two synthons was controlled using the alkylation of chiral bromoalienes derived from naturally occurring (S)-serine and (S)-phenyllactic acid. The cupration of bromoallenes derived from (S)-serine also provides a general method for the synthesis of chiral beta-alkylated aspartic acid derivatives. (C) 1997, Elsevier Science Ltd.
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页码:1447 / 1456
页数:10
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