title: Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin.
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.
authors: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto ON M5S 3H6, Canada.
authors: Thomas M
authors: TM
authors: Beale
authors: Mark S
authors: MS
authors: Taylor
mesh_terms: D001889:Borinic Acids / Q000737:chemistry; D002301:Cardiac Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004070:Digitalis / Q000737:chemistry; D004074:Digitoxin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001889:Borinic Acids; D002301:Cardiac Glycosides; D004074:Digitoxin