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)

Full text not available in this repository.Request a copy

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;
  • Item type:Article
    ID code:38961
    Dates:
    Date
    Event
    2004
    Published
    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
CORE (COnnecting REpositories)