Next Article in Journal
In Vitro Evaluation of Cytotoxicity and Permeation Study on Lysine- and Arginine-Based Lipopeptides with Proven Antimicrobial Activity
Next Article in Special Issue
Nucleobase–Guanidiniocarbonyl-Pyrrole Conjugates as Novel Fluorimetric Sensors for Single Stranded RNA
Previous Article in Journal
Chemical Constituents from Euphorbia kansui
Previous Article in Special Issue
Multi Component Reactions under Increased Pressure: On the Mechanism of Formation of Pyridazino[5,4,3-de][1,6]naphthyridine Derivatives by the Reaction of Malononitrile, Aldehydes and 2-Oxoglyoxalarylhydrazones in Q-Tubes
Open AccessCommunication

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.
Molecules 2017, 22(12), 2171; https://doi.org/10.3390/molecules22122171
Received: 30 October 2017 / Revised: 5 December 2017 / Accepted: 7 December 2017 / Published: 8 December 2017
(This article belongs to the Collection Heterocyclic Compounds)
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
Show Figures

Graphical abstract

MDPI and ACS Style

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.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Search more from Scilit
 
Search
Back to TopTop