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

Audouard, Christophe and Fawcett, John and Griffith, Gerry A and Kerouredan, Erwan and Miah, Afjal Hussain and Percy, Jonathan and Yang, Hongli (2004) A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses. Organic Letters, 6 (23). pp. 4269-4272. ISSN 1523-7060 (https://doi.org/10.1021/ol0482902)

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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 sodium borohydride delivers diols, which undergo RCM smoothly to afford cyclohexene diols.

ORCID iDs

Audouard, Christophe, Fawcett, John, Griffith, Gerry A, Kerouredan, Erwan, Miah, Afjal Hussain, Percy, Jonathan ORCID logoORCID: https://orcid.org/0000-0001-8636-2704 and Yang, Hongli;
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