HIGHLY STEREOCONTROLLED ASYMMETRIC SYNTHESES OF TAXOL AND TAXOTERE C-13 SIDE-CHAIN ANALOGS

被引:32
作者
MUKAI, C [1 ]
KIM, IJ [1 ]
FURU, E [1 ]
HANAOKA, M [1 ]
机构
[1] KANAZAWA UNIV,FAC PHARMACEUT SCI,TAKARA MACHI,KANAZAWA,ISHIKAWA 920,JAPAN
关键词
D O I
10.1016/S0040-4020(01)81916-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric aldol reaction of (+)-tricarbonyl(eta6-2-trimethylsilylbenzaldehyde)chromium(0) complex (4) with titanium enolate of S-tert-butyl benzyloxyethanethioate (10) provided, after consecutive desilylation and decomplexation, anti-aldol product 15 in a highly stereoselective manner. Anti-product 15 was subsequently converted to (2R,3S)-N-benzoyl- and N-tert-butoxycarbonyl-3-phenylisoserine methyl esters (23 and 24), C-13 side chain analogues of taxol (1) and taxotere (2).
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页码:8323 / 8336
页数:14
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