From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence

A Barbier reaction–Heck arylation sequence from α-bromomethylbutenolide to fused tri and tetracyclic lactones has been developed. The first step involving a Barbier reaction enabled installing ortho-bromoaromatics in α-ylidene γ-lactones. The latter substrates were subjected to intramolecular Heck r...

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Detalles Bibliográficos
Autores principales: Talbi, Arbia, Gaucher, Anne, Bourdreux, Flavien, Marrot, Jérôme, Efrit, Mohamed L., M’Rabet, Hédi, Prim, Damien
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149967/
https://www.ncbi.nlm.nih.gov/pubmed/29292736
http://dx.doi.org/10.3390/molecules22122171
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author Talbi, Arbia
Gaucher, Anne
Bourdreux, Flavien
Marrot, Jérôme
Efrit, Mohamed L.
M’Rabet, Hédi
Prim, Damien
author_facet Talbi, Arbia
Gaucher, Anne
Bourdreux, Flavien
Marrot, Jérôme
Efrit, Mohamed L.
M’Rabet, Hédi
Prim, Damien
author_sort Talbi, Arbia
collection PubMed
description A Barbier reaction–Heck arylation sequence from α-bromomethylbutenolide to fused tri and tetracyclic lactones has been developed. The first step involving a Barbier reaction enabled installing ortho-bromoaromatics in α-ylidene γ-lactones. The latter substrates were subjected to intramolecular Heck reaction conditions which selectively afforded 6,5,5 or 6,6,5 fused ring systems depending on the nature of the base employed.
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spelling pubmed-61499672018-11-13 From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence Talbi, Arbia Gaucher, Anne Bourdreux, Flavien Marrot, Jérôme Efrit, Mohamed L. M’Rabet, Hédi Prim, Damien Molecules Communication A Barbier reaction–Heck arylation sequence from α-bromomethylbutenolide to fused tri and tetracyclic lactones has been developed. The first step involving a Barbier reaction enabled installing ortho-bromoaromatics in α-ylidene γ-lactones. The latter substrates were subjected to intramolecular Heck reaction conditions which selectively afforded 6,5,5 or 6,6,5 fused ring systems depending on the nature of the base employed. MDPI 2017-12-08 /pmc/articles/PMC6149967/ /pubmed/29292736 http://dx.doi.org/10.3390/molecules22122171 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Talbi, Arbia
Gaucher, Anne
Bourdreux, Flavien
Marrot, Jérôme
Efrit, Mohamed L.
M’Rabet, Hédi
Prim, Damien
From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence
title From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence
title_full From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence
title_fullStr From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence
title_full_unstemmed From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence
title_short From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence
title_sort from α-bromomethylbutenolide to fused tri(tetra) cyclic dihydrofurandiones through barbier reaction–heck arylation sequence
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149967/
https://www.ncbi.nlm.nih.gov/pubmed/29292736
http://dx.doi.org/10.3390/molecules22122171
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