title: Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile.
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.
authors.affiliation: Department of Chemistry, University of Leicester, University Road, Leicester, UK.
authors.forename: Andrea
authors.initials: A
authors.lastname: Arany
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Crowley
authors.forename: John
authors.initials: J
authors.lastname: Fawcett
authors.forename: Michael B
authors.initials: MB
authors.lastname: Hursthouse
authors.forename: Benson M
authors.initials: BM
authors.lastname: Kariuki
authors.forename: Mark E
authors.initials: ME
authors.lastname: Light
authors.forename: Andrew C
authors.initials: AC
authors.lastname: Moralee
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: Percy
authors.forename: Vittoria
authors.initials: V
authors.lastname: Salafia