Studies on the total synthesis of natural alkaloid 6-exo-(acetyoxy)-8-azabicyclo[3.2.1]-octan-2-exo-ol(II) -: The synthesis of an intermediate, 8-methyl-2β-hydroxy-8-azabicyclo[3.2.1.]octane-6-exo-carbonitrile

被引:0
|
作者
Zeng, LM [1 ]
Yang, SM [1 ]
Su, JY [1 ]
Wu, JQ [1 ]
Wan, YQ [1 ]
机构
[1] Zhongshan Univ, Dept Chem, Guangzhou 510275, Peoples R China
来源
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE | 1998年 / 19卷 / 05期
关键词
6-exo-(acetyoxy)-8-azabicyclo[3.2.1]-octan-2-exo-ol; 1,3-dipolar cycloaddition; synthesis; 8-methyl-2 beta-hydroxy-8-azabicyclo[3.2.1]octane-6-exo-carbonitrile;
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of N-methyl-3-hydroxypyridinium iodide with acrylonitrile has been studied. Under various reaction conditions, none of the desired cycloaddition product was resulted. Instead, a Michael addition product was obtained. Alternatively, the 1,3-dipolar cycloaddition was achieved by the reaction of N-methyl-3-oxopyridinium betaine with acrylonitrile in THF with a high regioselectivity and stereoselectivity. This paper reports the synthesis of an intermediate 8-methyl-2 beta-hydroxy-8-azabicyclo [3.2.1]octane-6-exo-carbonitrile of 6-exo-(acetyoxy)-8-azabicyclo[3.2.1]-octan-2-exo-ol. This synthetic route involves two high stereoselective steps.
引用
收藏
页码:737 / 740
页数:4
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