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.
- Stille coupling
- difluorinated cyclohexenol
Arany, A., Crowley, P. J., Fawcett, J., Hursthouse, M. B., Kariuki, B. M., Light, M. E., Moralee, A. C., Percy, J., & Salafia, V. (2004). Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile. Organic and Biomolecular Chemistry, 2(4), 455-465 . https://doi.org/10.1039/b314314g