A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses

C Audouard, J Fawcett, GA Griffith, E Kérourédan…

Index: Audouard, Christophe; Fawcett, John; Griffith, Gerry A.; Kerouredan, Erwan; Miah, Afjal; Percy, Jonathan M.; Yang, Hongli Organic Letters, 2004 , vol. 6, # 23 p. 4269 - 4272

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Citation Number: 29

Abstract

Direct precursors to analogues of pentopyranoses, 6-deoxyhexoses, and hexoses, in which a CF2 center replaces the pyranose oxygen, have been synthesized rapidly from trifluoroethanol. A simple scaleable allylation reaction delivers ethers which undergo dehydrofluorination/metalation, followed by addition to either acrolein or cinnamaldehyde, to afford allylic alcohols. Fluorine-assisted [3, 3]-rearrangement followed by reduction with ...

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