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

A Arany; PJ Crowley; J Fawcett; MB Hursthouse; Benson Kariuki; ME Light; Andrew Moralee; Jonathan Percy; Vittoria Salafia

doi:10.1039/b314314g

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

A Arany, PJ Crowley, J Fawcett, MB Hursthouse, Benson Kariuki, ME Light, Andrew Moralee, Jonathan Percy, Vittoria Salafia

Chemistry

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16 Citations (Scopus)

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 language	English
Pages (from-to)	455-465
Number of pages	11
Journal	Organic and Biomolecular Chemistry
Volume	2
DOIs	https://doi.org/10.1039/b314314g
Publication status	Published - 1 Jan 2004

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

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.",

author = "A Arany and PJ Crowley and J Fawcett and MB Hursthouse and Benson Kariuki and ME Light and Andrew Moralee and Jonathan Percy and Vittoria Salafia",

year = "2004",

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doi = "10.1039/b314314g",

language = "English",

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T1 - Highly functionalised difluorinated (hydroxymethyl)-conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile

AU - Arany, A

AU - Crowley, PJ

AU - Fawcett, J

AU - Hursthouse, MB

AU - Kariuki, Benson

AU - Light, ME

AU - Moralee, Andrew

AU - Percy, Jonathan

AU - Salafia, Vittoria

PY - 2004/1/1

Y1 - 2004/1/1

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/1342344957

U2 - 10.1039/b314314g

DO - 10.1039/b314314g

M3 - Article

C2 - 14770223

VL - 2

SP - 455

EP - 465

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

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

Abstract

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