Synthesis of Cardiac Glycoside Analogs by Catalyst-Controlled, Regioselective Glycosylation of Digitoxin

被引：72

作者：

Beale, Thomas M. ^{[1
]}

Taylor, Mark S. ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 06期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

NATURAL-PRODUCTS; STEREOSELECTIVE-SYNTHESIS; CHEMICAL-SYNTHESIS; BUILDING-BLOCKS; HYDROXY-GROUPS; CELL-CULTURES; DERIVATIVES; GLYCOSYLTRANSFERASES; BIOTRANSFORMATION; HEXOPYRANOSIDES;

D O I：

10.1021/ol4003042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cardiac glycoside natural product digitoxin was selectively glycosylated at one of its five hydroxyl groups using a borinic acid derived catalyst. This method provided access to the glycosylation pattern characteristic of a subclass of natural products from Digitalis purpurea. Variation of the glycosyl donor was tolerated, enabling the synthesis of novel cardiac glycoside analogs from readily available materials.

引用

页码：1358 / 1361

页数：4

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