First enantioselective total synthesis of (-)-centrolobine

被引：86

作者：

Colobert, F

Des Mazery, R

Solladié, G

Carreño, MC

机构：

[1] Univ Strasbourg 1, CNRS, Lab Stereochim, ECPM, F-67087 Strasbourg 2, France

[2] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 10期

关键词：

D O I：

10.1021/ol025778z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The first enantioselective total synthesis of (-)-Centrolobine is described. The key reaction is the synthesis of the cis-disubstituted tetrahydropyran framework by intramolecular cyclization of the enantiopure hydroxyketone 3 with Et3SiH and TMSOTf. The stereoselective reduction of the beta-ketosulfoxide 4 is the source of chirality. Revision of the absolute configuration of (-)-Centrolobine is proposed.

引用

页码：1723 / 1725

页数：3

共 28 条

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[2]

[Anonymous], GAZZ CHIM ITAL

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