Synthetic studies on (+)-biotin, Part 11:: Application of Cinchona alkaloid-mediated asymmetric alcoholysis of meso-cyclic anhydride in the total synthesis of (+)-biotin

被引：24

作者：

Dai, Hui-Fang ^{[1
]}

Chen, Wen-Xue ^{[1
]}

Zhao, Lei ^{[2
]}

Xiong, Fei ^{[2
]}

Sheng, Hao ^{[2
]}

Chen, Fen-Er ^{[1
,2
]}

机构：

[1] Fudan Univ, Fudan DSM Joint Lab Synthet Method & Chiral Techn, Shanghai 200433, Peoples R China

[2] Fudan Univ, Inst Biomed Sci, Shanghai 200031, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 10期

关键词：

anion exchange resin D296; asymmetric alcoholysis; (+)-biotin; Cinchona alkaloids; Fukuyama-type cross-coupling; palladium nanoparticles;

D O I：

10.1002/adsc.200800151

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A practical and asymmetric process for the total synthesis of (+)-biotin (1) has been accomplished starting from cis- 1,3 -dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid (2). This approach features a highly enantioselective alcoholysis of mesocyclic anhydride 3 into (4S,5R)-cinnamyl hemiester 4 mediated by Cinchona alkaloids. Another attractive feature of this synthesis involves the use of recyclable palladium nanoparticles-catalyzed assembly of the 4-carboxybutyl chain at C-4 in (3aS,6aR)thiolactone 7 employing an improved Fukuyama-type cross-coupling reaction

引用

页码：1635 / 1641

页数：7

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