THE CHEMISTRY OF TAXANES - REACTION OF TAXOL AND BACCATIN DERIVATIVES WITH LEWIS-ACIDS IN APROTIC AND PROTIC MEDIA

被引:60
作者
CHEN, SH
HUANG, S
WEI, JM
FARINA, V
机构
[1] Bristol-Myers Squibb, Pharmaceutical Research Institute, Wallingford, CT 06492-7660
关键词
D O I
10.1016/S0040-4020(01)80381-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several Lewis acids were shown to cleanly open the oxetane ring of taxol and baccatin derivatives. The reaction is shown to proceed via anchimeric assistance by the C-4 acetate group. Several minor products, including a novel derivative possessing a bridged C-ring, were also isolated. A mechanistic rationale is provided for all compounds formed. When taxol derivatives were treated with Lewis acids in methanol, ester cleavage reactions were observed. We provide conditions that are selective for C-10 acetate cleavage and for C-13 side-chain methanolysis.
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页码:2805 / 2828
页数:24
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