The Journal of organic chemistry

De Novo Approach to 2-Deoxy-β-glycosides: Asymmetric Syntheses of Digoxose and Digitoxin1

M Zhou, GA O'Doherty

Index: Zhou, Maoquan; O'Doherty, George A. Journal of Organic Chemistry, 2007 , vol. 72, # 7 p. 2485 - 2493

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Citation Number: 83

Abstract

A highly enantioselective and straightforward route to trisaccharide natural products digoxose and digitoxin has been developed. Key to this approach is the iterative application of the palladium-catalyzed glycosylation reaction, reductive 1, 3-transposition, diastereoselective dihydroxylation, and regioselective protection. The first total synthesis of natural product digoxose was accomplished in 19 total steps from achiral 2-acylfuran, and ...

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