Issue 4, 2004
From the journal:

Organic & Biomolecular Chemistry

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

Andrea Arany,a   Patrick J. Crowley,b   John Fawcett,c   Michael B. Hursthouse,d   Benson M. Kariuki,a   Mark E. Light,d   Andrew C. Moralee,c   Jonathan M. Percy*c  and  Vittoria Salafiac  

* Corresponding authors

a School of Chemical Sciences, University of Birmingham, Edgbaston, Birmingham, UK

b Syngenta Ltd., Jealott's Hill International Research Centre, Bracknell, Berks, UK

c Department of Chemistry, University of Leicester, University Road, Leicester, UK
E-mail: jmp29@le.ac.uk
Fax: +44 116 252 3789
Tel: +44 116 252 2140

d EPSRC National X-Ray Crystallography Service, Department of Chemistry, University of Southampton, Highfield, Southampton, UK

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.

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

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Article information

DOI
https://doi.org/10.1039/B314314G
Article type
Paper
Submitted
10 Nov 2003
Accepted
03 Dec 2003
First published
21 Jan 2004

Org. Biomol. Chem., 2004,2, 455-465

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

A. Arany, P. J. Crowley, J. Fawcett, M. B. Hursthouse, B. M. Kariuki, M. E. Light, A. C. Moralee, J. M. Percy and V. Salafia, Org. Biomol. Chem., 2004, 2, 455 DOI: 10.1039/B314314G

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