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Molecules 2017, 22(12), 2171; https://doi.org/10.3390/molecules22122171

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

1
Laboratoire de Synthèse Organique Sélective et Hétérocyclique-Evaluation de l’Activité Biologique, Faculté des Sciences de Tunis, Université de Tunis El Manar, Tunis 2092, Tunisie
2
Institut Lavoisier de Versailles, Université Paris-Saclay, UVSQ, CNRS, 78035 Versailles, France
*
Authors to whom correspondence should be addressed.
Received: 30 October 2017 / Revised: 5 December 2017 / Accepted: 7 December 2017 / Published: 8 December 2017
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

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. View Full-Text
Keywords: bromomethylbutenolide; tri(tetra)cyclic architectures; Barbier; intramolecular Heck reaction bromomethylbutenolide; tri(tetra)cyclic architectures; Barbier; intramolecular Heck reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Talbi, A.; Gaucher, A.; Bourdreux, F.; Marrot, J.; Efrit, M.L.; M’Rabet, H.; Prim, D. From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence. Molecules 2017, 22, 2171.

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