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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Silvestre, Virginie Despiau, Carole F. Boussonnière, Anne Dénès, Fabrice Bénéteau, Romain Lebreton, Jacques Rouaud, Jean-christophe |
| Description | Author Affiliation: Bénéteau R ( CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssiniere BP 92208-44322, Nantes Cedex 3 (France).); Despiau CF ( CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssiniere BP 92208-44322, Nantes Cedex 3 (France).); Rouaud JC ( CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssiniere BP 92208-44322, Nantes Cedex 3 (France).); Boussonnière A ( CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssiniere BP 92208-44322, Nantes Cedex 3 (France).); Silvestre V ( Current Address: Université du Maine and CNRS UMR 6283, Institut des Molécules et Matériaux du Mans, Faculté des Sciences et Techniques, avenue Olivier Messiaen, 72085 Le Mans Cedex 9 (France).); Lebreton J ( CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssiniere BP 92208-44322, Nantes Cedex 3 (France).); Dénès F ( CEISAM UMR 6230 - UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssiniere BP 92208-44322, Nantes Cedex 3 (France).) |
| Abstract | Polysubstituted butenolides were obtained in good to high yields from α-bromoesters derived from propargyl alcohols by a one-pot reaction involving the radical cyclization of α-bromo aluminium acetals, followed by the oxidation of the resulting cyclic aluminium acetals in an Oppenauer-type process and migration of the exocyclic CC bond into the α,β-position. Comparison with the direct cyclization of α-bromoesters at high temperature and under high dilution conditions is described. Deuterium-labelling experiments allowed us to uncover “invisible” 1,5-hydrogen atom transfers (1,5-HATs) that occur during these cyclization processes, together with the consequences of the latter in the epimerization of stereogenic centres. Compared to the classical approach, the cyclization of aluminium acetals proved to be highly chemoselective and its efficiency was illustrated by the short total syntheses of optically enriched γ-butenolides isolated from Plagiomnium undulatum and from Kyrtuhrix maculans. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 32 |
| Volume Number | 21 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2015-08-03 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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