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

页码：737 / 740

页数：4

共 8 条

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