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

Andrea Arany; Patrick J Crowley; John Fawcett; Michael B. Hursthouse; Benson M Kariuki; Mark E. Light; Andrew C Moralee; Jonathan Percy; Vittoria Salafia

doi:10.1039/b314314g

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

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

Pure And Applied Chemistry

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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.

Original language	English
Pages (from-to)	455-465
Number of pages	11
Journal	Organic and Biomolecular Chemistry
Volume	2
Issue number	4
DOIs	https://doi.org/10.1039/b314314g
Publication status	Published - 2004

Keywords

difluorodienophile
Stille coupling
ring-opening
difluorinated cyclohexenol

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10.1039/b314314g

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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.",

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author = "Andrea Arany and Crowley, {Patrick J} and John Fawcett and Hursthouse, {Michael B.} and Kariuki, {Benson M} and Light, {Mark E.} and Moralee, {Andrew C} and Jonathan Percy and Vittoria Salafia",

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doi = "10.1039/b314314g",

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

AU - Arany, Andrea

AU - Crowley, Patrick J

AU - Fawcett, John

AU - Hursthouse, Michael B.

AU - Kariuki, Benson M

AU - Light, Mark E.

AU - Moralee, Andrew C

AU - Percy, Jonathan

AU - Salafia, Vittoria

PY - 2004

Y1 - 2004

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.

KW - difluorodienophile

KW - Stille coupling

KW - ring-opening

KW - difluorinated cyclohexenol

U2 - 10.1039/b314314g

DO - 10.1039/b314314g

M3 - Article

SN - 1477-0520

VL - 2

SP - 455

EP - 465

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 4

ER -

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

Abstract

Keywords

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