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

doi:10.1021/ol0482902

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

27 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 language	English
Pages (from-to)	4269-4272
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	23
DOIs	https://doi.org/10.1021/ol0482902
Publication status	Published - 2004

Keywords

pentopyranoses
6-deoxyhexoses
hexoses

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10.1021/ol0482902

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

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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author = "Christophe Audouard and John Fawcett and Griffith, {Gerry A} and Erwan Kerouredan and Miah, {Afjal Hussain} and Jonathan Percy and Hongli Yang",

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doi = "10.1021/ol0482902",

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journal = "Organic Letters",

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T1 - A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses

AU - Audouard, Christophe

AU - Fawcett, John

AU - Griffith, Gerry A

AU - Kerouredan, Erwan

AU - Miah, Afjal Hussain

AU - Percy, Jonathan

AU - Yang, Hongli

PY - 2004

Y1 - 2004

N2 - 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.

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.

KW - pentopyranoses

KW - 6-deoxyhexoses

KW - hexoses

U2 - 10.1021/ol0482902

DO - 10.1021/ol0482902

M3 - Article

SN - 1523-7060

VL - 6

SP - 4269

EP - 4272

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

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

Abstract

Keywords

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