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

Autor: Arbia Talbi, Anne Gaucher, Flavien Bourdreux, Jérôme Marrot, Mohamed L. Efrit, Hédi M’Rabet, Damien Prim
Jazyk: angličtina
Rok vydání: 2017
Předmět:
Zdroj: Molecules, Vol 22, Iss 12, p 2171 (2017)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules22122171
Popis: 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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