Stereoselective entry to 1′-C-branched 4′-thionucleosides from 4′-thiofuranoid glycal:: synthesis of 4′-thioangustmycin C

被引:21
作者
Haraguchi, K [1 ]
Takahashi, H [1 ]
Tanaka, H [1 ]
机构
[1] Showa Univ, Sch Pharmaceut Sci, Shinagawa Ku, Tokyo 1428555, Japan
关键词
nucleosides; glycals; glycosidation; antibiotics;
D O I
10.1016/S0040-4039(02)01131-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereoselective synthetic method for the synthesis of novel 1'-C-carbon-substituted 4'-thionucleosides has been developed. The present method consists of the following steps: (1) preparation of the 1-C-carbon-substituted 4-thiofuranoid glycals based on lithiation, and (2) NIS- or PhSeCl-initiated stereoselective glycosidation to these 1-substituted glycals. This synthetic sequence enabled us to synthesize the 4'-thio analogue of antitumor antibiotic angustmycin (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5657 / 5660
页数:4
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