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
收藏
页码：3157 / 3167
页数：11
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