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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, 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: 04 Jun 2017 04:59
URI: http://orca-mwe.cf.ac.uk/id/eprint/47209

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