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Jean-Gerard, L., Mace, F., Ngo, A. N., Pauvert, M., Dentel, H., Evain, M., Collet, S. & Guingant, A. (2012) Remote Control of the C-3-C-4 Double-Bond Epoxidation of a Chiral 1,2-Dihydroquinoline: Application to the Synthesis of (-)-(R)-Sumanirole (PNU-95666E). Eur. J. Org. Chem. 4240–4248.
Added by: Laurent Cournède (2016-03-10 21:28:38) |
| Type de référence: Article DOI: 10.1002/ejoc.201200344 Numéro d'identification (ISBN etc.): 1434-193X Clé BibTeX: JeanGerard2012 Voir tous les détails bibliographiques  |
Catégories: MIOPS Mots-clés: 1, 2, 3, 4-tetrahydroquinolines, anachelin, analogs, Asymmetric synthesis, asymmetric-synthesis, chemistry, Epoxidation, hydrogenation, Nitrogen heterocycles, nmda receptor, reissert compounds, sumanirole, Total synthesis Créateurs: Collet, Dentel, Evain, Guingant, Jean-Gerard, Mace, Ngo, Pauvert Collection: Eur. J. Org. Chem. |
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A twelve-step synthesis of ()-(R)-sumanirole starting from quinoline is described. The first synthetic approach, using a chiral Reissert adduct, was too problematic to be pursued further. In the second successful approach, the authors took advantage of the stereoselective epoxidation of a 1,2-dihydroquinoline bearing an Evans' chiral auxiliary at N-1.
Added by: Laurent Cournède |