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

Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile
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.
myo-inositol 1, 4, 5-trisphosphate, 2-fluoroacrylic acid-derivatives, ring-opening reactions, fluorine substitution, chemical consequences, difluorocyclopentane derivatives, dipeptide isosteres, facile synthesis
1477-0520
455-465
Arany, Andrea
217fb728-b3c1-4011-90c8-bfc0a6ea533c
Crowley, Patrick J.
2f68e334-3bb8-40db-af3b-9cc8c9973799
Fawcett, John
20eb6e74-26e0-4569-a689-4737cdf8f4a6
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Kariuki, Benson M.
634ee7db-bcd1-4544-b667-2ad8c48ecedd
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Moralee, Andrew C.
6fca431a-571c-4296-bb96-83bde0a8a727
Percy, Jonathan M.
2e5ad3da-e361-4521-a28f-acb97e4e9118
Salafia, Vittoria
e3e3c0e9-c5d3-45fb-bf23-e7bce321b4c9
Arany, Andrea
217fb728-b3c1-4011-90c8-bfc0a6ea533c
Crowley, Patrick J.
2f68e334-3bb8-40db-af3b-9cc8c9973799
Fawcett, John
20eb6e74-26e0-4569-a689-4737cdf8f4a6
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Kariuki, Benson M.
634ee7db-bcd1-4544-b667-2ad8c48ecedd
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Moralee, Andrew C.
6fca431a-571c-4296-bb96-83bde0a8a727
Percy, Jonathan M.
2e5ad3da-e361-4521-a28f-acb97e4e9118
Salafia, Vittoria
e3e3c0e9-c5d3-45fb-bf23-e7bce321b4c9

Arany, Andrea, Crowley, Patrick J., Fawcett, John, Hursthouse, Michael B., Kariuki, Benson M., Light, Mark E., Moralee, Andrew C., Percy, Jonathan M. and Salafia, Vittoria (2004) Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile. Organic and Biomolecular Chemistry, 2 (4), 455-465. (doi:10.1039/b314314g).

Record type: Article

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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More information

Published date: 2004
Keywords: myo-inositol 1, 4, 5-trisphosphate, 2-fluoroacrylic acid-derivatives, ring-opening reactions, fluorine substitution, chemical consequences, difluorocyclopentane derivatives, dipeptide isosteres, facile synthesis

Identifiers

Local EPrints ID: 39105
URI: https://eprints.soton.ac.uk/id/eprint/39105
ISSN: 1477-0520
PURE UUID: ea4bc1bd-534f-4496-9156-8d8f92f3533f
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 21 Jun 2006
Last modified: 06 Jun 2018 12:54

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Contributors

Author: Andrea Arany
Author: Patrick J. Crowley
Author: John Fawcett
Author: Benson M. Kariuki
Author: Mark E. Light ORCID iD
Author: Andrew C. Moralee
Author: Jonathan M. Percy
Author: Vittoria Salafia

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