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Issue 4, 2004
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Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels–Alder reactions of a difluorinated dienophile

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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.

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

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Publication details

The article was received on 10 Nov 2003, accepted on 03 Dec 2003 and first published on 21 Jan 2004


Article type: Paper
DOI: 10.1039/B314314G
Citation: Org. Biomol. Chem., 2004,2, 455-465
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    Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels–Alder reactions of a difluorinated dienophile

    A. Arany, P. J. Crowley, J. Fawcett, M. B. Hursthouse, B. M. Kariuki, M. E. Light, A. C. Moralee, J. M. Percy and V. Salafia, Org. Biomol. Chem., 2004, 2, 455
    DOI: 10.1039/B314314G

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