SYNTHESIS OF THE AZIRIDINO[1,2-A]PYRROLIDINE SUBSTRUCTURE OF THE ANTITUMOR AGENTS AZINOMYCIN-A AND AZINOMYCIN-B

被引:62
作者
COLEMAN, RS
CARPENTER, AJ
机构
[1] Department of Chemistry and Biochemistry, University of South Carolina, Columbia
关键词
D O I
10.1021/jo00048a006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereoselective synthesis of the central aziridino[1,2-alpha]pyrrolidine substructure (19) of the antitumor agents azinomycin A and B is reported and featured as the key step an intramolecular Michael addition-elimination reaction between the aziridine and beta-bromo acrylate of intermediate 18; this compound was efficiently constructed via aldehyde 14, which was prepared from D-glucosamine.
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页码:5813 / 5815
页数:3
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