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

Research output: Contribution to journalArticle

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.
LanguageEnglish
Pages4269-4272
Number of pages4
JournalOrganic Letters
Volume6
Issue number23
DOIs
Publication statusPublished - 2004

Fingerprint

hexoses
Allylation
Trifluoroethanol
Acrolein
Hexoses
Ethers
borohydrides
Fluorine
fluorine
ethers
alcohols
routes
sodium
analogs
Oxygen
oxygen
cyclohexene
cinnamic aldehyde
sodium borohydride
allyl alcohol

Keywords

  • pentopyranoses
  • 6-deoxyhexoses
  • hexoses

Cite this

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
Audouard, Christophe ; Fawcett, John ; Griffith, Gerry A ; Kerouredan, Erwan ; Miah, Afjal Hussain ; Percy, Jonathan ; Yang, Hongli. / A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses. In: Organic Letters. 2004 ; Vol. 6, No. 23. pp. 4269-4272 .
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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.",
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Audouard, C, Fawcett, J, Griffith, GA, Kerouredan, E, Miah, AH, Percy, J & Yang, H 2004, 'A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses' Organic Letters, vol. 6, no. 23, pp. 4269-4272 . https://doi.org/10.1021/ol0482902

A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses. / Audouard, Christophe; Fawcett, John; Griffith, Gerry A; Kerouredan, Erwan; Miah, Afjal Hussain; Percy, Jonathan; Yang, Hongli.

In: Organic Letters, Vol. 6, No. 23, 2004, p. 4269-4272 .

Research output: Contribution to journalArticle

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AU - Miah, Afjal Hussain

AU - Percy, Jonathan

AU - Yang, Hongli

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AB - 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.

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KW - 6-deoxyhexoses

KW - hexoses

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