A Glycal Approach to the Synthesis of Steviamine Analogues

被引：16

作者：

Santhanam, Venkatesan ^{[1
]}

Ramesh, Namakkal G. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, New Delhi 110016, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 31期

关键词：

Natural products; Nitrogen heterocycles; Alkaloids; Azasugars; Carbohydrates; Biological activity; Chiral pool; ALPHA-N-ACETYLGALACTOSAMINIDASE; (-)-STEVIAMINE; CYCLOADDITION; INHIBITION; DEFICIENCY; SCHINDLER; STRATEGY;

D O I：

10.1002/ejoc.201402943

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of two new stereoisomers of steviamine, namely 1,8a-di-epi-(+)-steviamine and 2,3-di-epi-(-)-steviamine, is reported, starting from tri-O-benzyl-D-glucal. The key step in the synthesis was a modified Julia olefination of a 2-formyl-polyhydroxy-pyrrolidine with a sulfone derived from ethyl acetoacetate. Glycosidase-inhibition studies revealed that 2,3-di-epi-(-)-steviamine is a selective inhibitor of a-galactosidase.

引用

页码：6992 / 6999

页数：8

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