Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids

被引：28

作者：

Alibés, R

Blanco, P

Casas, E

Closa, M

de March, P

Figueredo, M ^{[1
]}

Font, J

Sanfeliu, E

Alvarez-Larena, A

机构：

[1] Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Spain

[2] Univ Autonoma Barcelona, Unitat Cristallog, Bellaterra 08193, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 08期

关键词：

D O I：

10.1021/jo047867q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general strategy for the construction of the 1-azabicyclo[5.3.0]decane core of Stemona alkaloids is developed. Our diversity-oriented approach exploits 1,3-dipolar cycloaddition of five-membered cyclic nitrones to C-6 olefins, followed by N-O reductive cleavage and azepine closure. The use of various enantiopure pyrroline N-oxides allows for a practical, stereoselective preparation of several putative precursors of different Stemona alkaloids.

引用

页码：3157 / 3167

页数：11

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