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

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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.

Creators(s): 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;
Item type:Article
ID code:38961
Keywords:pentopyranoses, 6-deoxyhexoses, hexoses, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
Subjects:Science > Chemistry
Department:Faculty of Science > Pure and Applied Chemistry
Depositing user: Pure Administrator
Date deposited:04 Apr 2012 14:46
Last modified:20 Jan 2021 20:04
URI:https://strathprints.strath.ac.uk/id/eprint/38961
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