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Literature DB >> 16956221

A stereoselective synthesis of digitoxin and digitoxigen mono- and bisdigitoxoside from digitoxigenin via a palladium-catalyzed glycosylation.

Abstract

A convergent and stereocontrolled route to trisaccharide natural product digitoxin has been developed. The route is amenable to the preparation of both the digitoxigen mono- and bisdigitoxoside. This route featured the iterative application of the palladium-catalyzed glycosylation reaction, reductive 1,3-transposition, diastereoselective dihydroxylation, and regioselective protection. The natural product digitoxin was fashioned in 15 steps starting from digitoxigenin 2 and pyranone 8a or 18 steps from achiral acylfuran.

Entities: Chemical

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Year: 2006 PMID： 16956221 PMCID： PMC2527289 DOI： 10.1021/ol061683b

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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