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http://hdl.handle.net/2445/171721| Title: | Conjugate Addition of 2-Acetylindole Enolates to UnsaturatedOxazolopiperidone Lactams: Enantioselective Access to the Tetracyclic RingSystem of Ervitsine |
| Author: | Amat Tusón, Mercedes Checa Castaño, Begoña Llor Brunés, Núria Pérez Bosch, Maria Bosch Cartes, Joan |
| Keywords: | Lactames Alcaloides Síntesi orgànica Lactams Alkaloids Organic synthesis |
| Issue Date: | 2011 |
| Publisher: | Wiley-VCH |
| Abstract: | The stereochemical outcome of the conjugate addition reactions of 2-acetylindole enolates to unsaturated phenylglycinol-derived oxazolopiperidone lactams 1a-f is studied. After reduction of the 2-acylindole carbonyl group, the Michael adduct cis-6 underwent a Lewis acid-promoted intramolecular α-amidoalkylation, enantioselectively leading to the tetracyclic ring system of the indole alkaloid ervitsine Keywords: Lactams / Asymmetric synthesis / Cyclization / Michael addition / Heterocycles |
| Note: | Versió postprint del document publicat a: |
| It is part of: | European Journal of Organic Chemistry, 2011, p. 898-907 |
| URI: | http://hdl.handle.net/2445/171721 |
| ISSN: | 1434-193X |
| Appears in Collections: | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia) |
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