Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile |
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| Authors: | Arany Andrea Crowley Patrick J Fawcett John Hursthouse Michael B Kariuki Benson M Light Mark E Moralee Andrew C Percy Jonathan M Salafia Vittoria |
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| Affiliation: | Department of Chemistry, University of Leicester, University Road, Leicester, UK. |
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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. |
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