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

[thumbnail of highly_functionalised.pdf]
Preview
PDF
highly_functionalised.pdf
Final Published Version

Download (314kB)| 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.

    ORCID iDs

    Arany, Andrea, Crowley, Patrick J, Fawcett, John, Hursthouse, Michael B., Kariuki, Benson M, Light, Mark E., Moralee, Andrew C, Percy, Jonathan ORCID logoORCID: https://orcid.org/0000-0001-8636-2704 and Salafia, Vittoria;