From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction-Heck Arylation
Arbia Talbi1,2, Anne Gaucher3, Flavien Bourdreux4
1Laboratoire de Synthèse Organique Sélective et Hétérocyclique-Evaluation de l'Activité Biologique, Faculté des Sciences de Tunis, Université de Tunis El Manar, Tunis 2092, Tunisie. arbiatalbi1@gmail.com.
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.
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