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

Arany, Andrea and Crowley, Patrick J and Fawcett, John and Hursthouse, Michael B. and Kariuki, Benson M and Light, Mark E. and Moralee, Andrew C and Percy, Jonathan and Salafia, Vittoria (2004) Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile. Organic and Biomolecular Chemistry, 2 (4). pp. 455-465. ISSN 1477-0520 (https://doi.org/10.1039/b314314g)

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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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• Item metadata

  Item type:	Article
  ID code:	38959
  Dates:	Date Event 2004 Published
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	04 Apr 2012 14:41
  Last modified:	22 Aug 2024 00:36
  URI:	https://strathprints.strath.ac.uk/id/eprint/38959