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

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 -bromoaromatics in α-ylidene γ-lactones. The latter substrates were subjected to intramolecular Heck reacti...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2017-12, Vol.22 (12), p.2171
Hauptverfasser: Talbi, Arbia, Gaucher, Anne, Bourdreux, Flavien, Marrot, Jérôme, Efrit, Mohamed L, M'Rabet, Hédi, Prim, Damien
Format: Artikel
Sprache:eng
Schlagworte:
Barbier
bromomethylbutenolide
Communication
Furans - chemical synthesis
intramolecular Heck reaction
Lactones
Lactones - chemical synthesis
Molecular Structure
Substrates
tri(tetra)cyclic architectures
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Zusammenfassung: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 -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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules22122171