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
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
2004
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 & Biomolecular Chemistry, 2 (4), .
(doi:10.1039/b314314g).
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.
This record has no associated files available for download.
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: http://eprints.soton.ac.uk/id/eprint/39105
ISSN: 1477-0520
PURE UUID: ea4bc1bd-534f-4496-9156-8d8f92f3533f
Catalogue record
Date deposited: 21 Jun 2006
Last modified: 16 Mar 2024 03:04
Export record
Altmetrics
Contributors
Author:
Andrea Arany
Author:
Patrick J. Crowley
Author:
John Fawcett
Author:
Benson M. Kariuki
Author:
Andrew C. Moralee
Author:
Jonathan M. Percy
Author:
Vittoria Salafia
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics
