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

Christophe Audouard, John Fawcett, Gerry A Griffith, Erwan Kerouredan, Afjal Hussain Miah, Jonathan Percy, Hongli Yang

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26 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)4269-4272
Number of pages4
JournalOrganic Letters
Volume6
Issue number23
DOIs
Publication statusPublished - 2004

Keywords

  • pentopyranoses
  • 6-deoxyhexoses
  • hexoses

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    Audouard, C., Fawcett, J., Griffith, G. A., Kerouredan, E., Miah, A. H., Percy, J., & Yang, H. (2004). A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses. Organic Letters, 6(23), 4269-4272 . https://doi.org/10.1021/ol0482902