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

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 23期

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

页码：3667 / 3672

页数：6

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