Synthetic studies on d-biotin.: Part 7:: A practical asymmetric total synthesis of d-biotin via enantioselective reduction of meso-cyclic imide catalyzed by oxazborolidine

被引:41
作者
Chen, FE [1 ]
Dai, HF [1 ]
Kuang, YY [1 ]
Jia, HQ [1 ]
机构
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
关键词
D O I
10.1016/j.tetasy.2003.08.034
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A novel and convenient method for the stereoselective synthesis of d-biotin I starting from the commercially available cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid 2 has been developed. The key features of this synthesis include the enantioselective reduction of a meso-cyclic imide, mediated by a chiral oxazborolidine catalyst, derived from (1S,2S)-(+)-threo-l(4-nitrophenyl)-2-amino-1,3-propanediol and the direct introduction of a C-5 side chain to the (3aS,6aR)-thiolactone through a modified di-Grignard reaction. Eriantioselectivities of 98% in the oxazborolidine-catalyzed asymmetric reduction process have been achieved. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3667 / 3672
页数:6
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