Strathprints logo
Strathprints Home | Open Access | Browse | Search | User area | Copyright | Help | Library Home | SUPrimo

Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile

Arany, Andrea and Crowley, Patrick J and Fawcett, John and Hursthouse, Michael B. and Kariuki, Benson M and Light, Mark E. and Moralee, Andrew C and Percy, Jonathan and Salafia, Vittoria (2004) Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile. Organic and Biomolecular Chemistry, 2 (4). pp. 455-465. ISSN 1477-0520

[img]
Preview
PDF - Published Version
Download (307Kb) | Preview

    Abstract

    A difluorodienophile, synthesised using a Stille coupling reaction underwent tin(IV)-catalysed cycloaddition with three furans to afford oxa[2.2.1]bicycloheptenes in good yield. Reduction of ester and carbamate carbonyl groups and diol protection as the acetonide set the stage for palladium-catalysed hydrostannylation in two cases. Treatment of the stannanes with methyllithium triggered ring-opening to afford highly-functionalised difluorinated cyclohexenols which could be deprotected to afford (hydroxymethyl)conduritol analogues.

    Item type: Article
    ID code: 38959
    Keywords: difluorodienophile, Stille coupling, ring-opening, difluorinated cyclohexenol , Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
    Subjects: Science > Chemistry
    Department: Faculty of Science > Pure and Applied Chemistry
    Related URLs:
      Depositing user: Pure Administrator
      Date Deposited: 04 Apr 2012 15:41
      Last modified: 06 Sep 2014 13:50
      URI: http://strathprints.strath.ac.uk/id/eprint/38959

      Actions (login required)

      View Item

      Fulltext Downloads: