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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
Síntesi orgànica
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
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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