Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile

Andrea Arany, Patrick J Crowley, John Fawcett, Michael B. Hursthouse, Benson M Kariuki, Mark E. Light, Andrew C Moralee, Jonathan Percy, Vittoria Salafia

Research output: Contribution to journalArticle

14 Citations (Scopus)
208 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)455-465
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number4
DOIs
Publication statusPublished - 2004

Keywords

  • difluorodienophile
  • Stille coupling
  • ring-opening
  • difluorinated cyclohexenol

Fingerprint Dive into the research topics of 'Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile'. Together they form a unique fingerprint.

  • Cite this

    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