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

Vista senzilla d'ítem
dc.contributor.authorAmat Tusón, Mercedes
dc.contributor.authorCheca Castaño, Begoña
dc.contributor.authorLlor Brunés, Núria
dc.contributor.authorPérez Bosch, Maria
dc.contributor.authorBosch Cartes, Joan
dc.date.accessioned2020-11-04T10:09:21Z
dc.date.available2020-11-04T10:09:21Z
dc.date.issued2011
dc.date.updated2020-11-04T10:09:21Z
dc.description.abstractThe 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
dc.format.extent10 p.
dc.format.mimetypeapplication/pdf
dc.identifier.idgrec597767
dc.identifier.issn1434-193X
dc.identifier.urihttps://hdl.handle.net/2445/171721
dc.language.isoeng
dc.publisherWiley-VCH
dc.relation.isformatofVersió postprint del document publicat a:
dc.relation.ispartofEuropean Journal of Organic Chemistry, 2011, p. 898-907
dc.rights(c) Wiley-VCH, 2011
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.sourceArticles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
dc.subject.classificationLactames
dc.subject.classificationAlcaloides
dc.subject.classificationSíntesi orgànica
dc.subject.otherLactams
dc.subject.otherAlkaloids
dc.subject.otherOrganic synthesis
dc.titleConjugate Addition of 2-Acetylindole Enolates to UnsaturatedOxazolopiperidone Lactams: Enantioselective Access to the Tetracyclic RingSystem of Ervitsine
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/acceptedVersion

Fitxers

Paquet original

Mostrant 1 - 1 de 1
Miniatura
Nom:
597767.pdf
Mida:
273.11 KB
Format:
Adobe Portable Document Format
Descarregar

Col·leccions

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