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2011

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/171721

Conjugate Addition of 2-Acetylindole Enolates to UnsaturatedOxazolopiperidone Lactams: Enantioselective Access to the Tetracyclic RingSystem of Ervitsine

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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

Subject

Lactames, Alcaloides, Síntesi orgànica

Subject (English)

Lactams, Alkaloids, Organic synthesis

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia)

Citation

AMAT TUSÓN, Mercedes, et al. Conjugate Addition of 2-Acetylindole Enolates to UnsaturatedOxazolopiperidone Lactams: Enantioselective Access to the Tetracyclic RingSystem of Ervitsine. European Journal of Organic Chemistry. 2011. Vol. 898-907. ISSN 1434-193X. [consulted: 9 of August of 2026]. Available at: https://hdl.handle.net/2445/171721

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