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

Arany, A., Crowley, P. J., Fawcett, J., Hursthouse, M. B., Kariuki, Benson ORCID: https://orcid.org/0000-0002-8658-3897, Light, M. E., Moralee, A. C., Percy, J. M. and Salafia, V. 2004. Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile. Organic & Biomolecular Chemistry 2 (4) , pp. 455-465. 10.1039/B314314G

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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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Subjects:	Q Science > QD Chemistry
Publisher:	Royal Society of Chemistry
Last Modified:	24 Oct 2022 11:11
URI:	https://orca.cardiff.ac.uk/id/eprint/47209

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