Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels–Alder reactions of a difluorinated dienophile
Organic & Biomolecular Chemistry Pub Date: 2004-01-21 DOI: 10.1039/B314314G
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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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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