Synthetic studies on d-biotin, part 8:: An efficient chemoenzymatic approach to the asymmetric total synthesis of d-biotin via a polymer-supported PLE-mediated desymmetrization of meso-symmetic dicarboxylic esters

被引：30

作者：

Chen, FE ^{[1
]}

Chen, XX ^{[1
]}

Dai, HF ^{[1
]}

Kuang, YY ^{[1
]}

Xie, B ^{[1
]}

Zhao, JF ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 04期

关键词：

d-biotin; desymmetrization; enzyme catalysis; kinetic resolution; polymer-supported PLE; vitamin H;

D O I：

10.1002/adsc.200404311

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A practical chemoenzymatic method for the asymmetric total synthesis of d-biotin (1) starting from the commercially available cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid (2) has been developed. The key step of the synthesis is the highly enantioselective hydrolysis of meso-dicarboxylic esters by a polymer-supported pig liver esterase and introduction of a formyl group at the C-4 position in 4 via a Grignard reaction. The polymer-supported PLE can be recovered quantitatively from the reaction mixture by simple filtration and reused without significant loss of activity.

引用

页码：549 / 554

页数：6

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