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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

Publication date

2020-11-04T10:09:21Z

2020-11-04T10:09:21Z

2011

2020-11-04T10:09:21Z

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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

Document Type

Article

Accepted version

Language

English

Subjects and keywords

Lactames; Alcaloides; Síntesi orgànica; Lactams; Alkaloids; Organic synthesis

Publisher

Wiley-VCH

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Versió postprint del document publicat a:

European Journal of Organic Chemistry, 2011, p. 898-907

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DIDL MARC MARC_CCUC METS OAI_DC ORE QDC RDF

Rights

(c) Wiley-VCH, 2011

This item appears in the following Collection(s)

Farmacologia, Toxicologia i Química Terapèutica [675]

ISGlobal - Institut de Salut Global de Barcelona [60807]

Nutrició, Ciències de l'Alimentació i Gastronomia [778]