Synthesis and X-ray crystal structure of (-)-calicheamicinone

被引：21
|
作者：
Clive, DLJ [1 ]
Bo, YX
Selvakumar, N
McDonald, R
Santarsiero, BD
机构：
[1] Univ Alberta, Dept Chem, Xray Serv Lab, Edmonton, AB T6G 2G2, Canada
[2] Mol Struct Corp, The Woodlands, TX 77381 USA
来源：
TETRAHEDRON | 1999年 / 55卷 / 11期
基金：
加拿大自然科学与工程研究理事会;
关键词：
D O I：
10.1016/S0040-4020(98)01140-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diels-Alder reaction between ketene acetal 3 and the beta-nitroacrylate ester 12 of (-)-8-phenylmenthol gave optically pure ketone 17. This substance was modified in such a way as to remove the chiral auxiliary and afford the epimeric silyl ethers 20M and 20m. Following procedures worked out using racemic materials, both 20M and 20m were converted into optically pure (-)-calicheamicinone (1). This is a crystalline substance, and an X-ray structure determination was carried out. (C) 1999 Elsevier Science Ltd. Ail rights reserved.
引用
收藏
页码：3277 / 3290
页数：14
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