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  • Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin.

Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin.

Organic letters (2013-03-08)
Thomas M Beale, Mark S Taylor
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Digitoxin, ≥92% (HPLC), powder
Digitoxin, European Pharmacopoeia (EP) Reference Standard