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 ortho-bromoaromatics in α-ylidene γ-lactones. The latter substrates were subjected to intramolecular Heck r...
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| Format: | Article |
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MDPI AG
2017-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/12/2171 |
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| author | Arbia Talbi Anne Gaucher Flavien Bourdreux Jérôme Marrot Mohamed L. Efrit Hédi M’Rabet Damien Prim |
| author_facet | Arbia Talbi Anne Gaucher Flavien Bourdreux Jérôme Marrot Mohamed L. Efrit Hédi M’Rabet Damien Prim |
| author_sort | Arbia Talbi |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-13T01:06:44Z |
| format | Article |
| id | doaj.art-87ad8080cbba4bb08d3c6574cb3a82a5 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T01:06:44Z |
| publishDate | 2017-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-87ad8080cbba4bb08d3c6574cb3a82a52022-12-22T03:09:18ZengMDPI AGMolecules1420-30492017-12-012212217110.3390/molecules22122171molecules22122171From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation SequenceArbia Talbi0Anne Gaucher1Flavien Bourdreux2Jérôme Marrot3Mohamed L. Efrit4Hédi M’Rabet5Damien Prim6Laboratoire de Synthèse Organique Sélective et Hétérocyclique-Evaluation de l’Activité Biologique, Faculté des Sciences de Tunis, Université de Tunis El Manar, Tunis 2092, TunisieInstitut Lavoisier de Versailles, Université Paris-Saclay, UVSQ, CNRS, 78035 Versailles, FranceInstitut Lavoisier de Versailles, Université Paris-Saclay, UVSQ, CNRS, 78035 Versailles, FranceInstitut Lavoisier de Versailles, Université Paris-Saclay, UVSQ, CNRS, 78035 Versailles, FranceLaboratoire de Synthèse Organique Sélective et Hétérocyclique-Evaluation de l’Activité Biologique, Faculté des Sciences de Tunis, Université de Tunis El Manar, Tunis 2092, TunisieLaboratoire de Synthèse Organique Sélective et Hétérocyclique-Evaluation de l’Activité Biologique, Faculté des Sciences de Tunis, Université de Tunis El Manar, Tunis 2092, TunisieInstitut Lavoisier de Versailles, Université Paris-Saclay, UVSQ, CNRS, 78035 Versailles, FranceA 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.https://www.mdpi.com/1420-3049/22/12/2171bromomethylbutenolidetri(tetra)cyclic architecturesBarbierintramolecular Heck reaction |
| spellingShingle | Arbia Talbi Anne Gaucher Flavien Bourdreux Jérôme Marrot Mohamed L. Efrit Hédi M’Rabet Damien Prim From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence Molecules bromomethylbutenolide tri(tetra)cyclic architectures Barbier intramolecular Heck reaction |
| title | From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence |
| title_full | From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence |
| title_fullStr | From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence |
| title_full_unstemmed | From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence |
| title_short | From α-Bromomethylbutenolide to Fused Tri(Tetra) Cyclic Dihydrofurandiones through Barbier Reaction–Heck Arylation Sequence |
| title_sort | from α bromomethylbutenolide to fused tri tetra cyclic dihydrofurandiones through barbier reaction heck arylation sequence |
| topic | bromomethylbutenolide tri(tetra)cyclic architectures Barbier intramolecular Heck reaction |
| url | https://www.mdpi.com/1420-3049/22/12/2171 |
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