Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile.
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.
Arany
Andrea
A
Department of Chemistry, University of Leicester, University Road, Leicester, UK.
Crowley
Patrick J
PJ
Fawcett
John
J
Hursthouse
Michael B
MB
Kariuki
Benson M
BM
Light
Mark E
ME
Moralee
Andrew C
AC
Percy
Jonathan M
JM
Salafia
Vittoria
V