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BIBTEX RIS

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

2004; Royal Society of Chemistry; Volume: 2; Issue: 4 Linguagem: Inglês

10.1039/b314314g

ISSN

1477-0539

Autores

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

Tópico(s)

Synthesis and Biological Evaluation

Resumo

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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