First stereocontrolled synthesis of (S)-cleonin and related cyclopropyl-substituted amino acids

被引：33
作者：
Esposito, A
Piras, PP
Ramazzotti, D
Taddel, M
机构：
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
[2] Univ Cagliari, Dipartimento Sci Chim, I-09042 Monserrato, CA, Italy
来源：
ORGANIC LETTERS | 2001年 / 3卷 / 21期
关键词：
D O I：
10.1021/ol016477c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Enantiomerically pure (S)-cleonin, a key component of the antitumor antibiotic cleomycin, was prepared starting from (R)-serine. The Kulinkovich cyclopropanation of the methyl ester of N-Cbz serine acetonide gave the hydroxycyclopropyl moiety. The amino alcohol region was further oxidized to amino acid. The Kulinkovich cyclopropanation allowed also the preparation of other non-natural substituted cyclopropylglycines.
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页码：3273 / 3275
页数：3
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