Conjugate Addition to Phenylglycinol-Derived Unsaturated ä-Lactams. Enantioselective Synthesos of Uleine Alkaloids

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dc.contributor.authorAmat Tusón, Mercedes
dc.contributor.authorPérez Bosch, Maria
dc.contributor.authorLlor Brunés, Núria
dc.contributor.authorEscolano Mirón, Carmen
dc.contributor.authorLuque Garriga, F. Xavier
dc.contributor.authorMolins i Grau, Elies
dc.contributor.authorBosch Cartes, Joan
dc.date.accessioned2020-05-13T07:01:29Z
dc.date.available2020-05-13T07:01:29Z
dc.date.issued2004-11-06
dc.date.updated2020-05-13T07:01:29Z
dc.description.abstractThe stereochemical outcome of the conjugate addition of a variety of stabilized nucleophiles (2indoleaceticenolatesandsulfur-stabilizedanions)tothephenylglycinol-derivedunsaturatedlactams trans-2, cis-2, and its 8-ethyl-substituted analogue 10 is studied. The factors governing the exo or endo facial stereoselectivity are discussed. This methodology provides short synthetic routes to either cis- ortrans-3,4-disubstituted enantiopure piperidines as well as efficient routes for the enantioselective construction of the tetracyclic ring system of uleine alkaloids, both in the normal and 20-epi series. The formal total synthesis of several alkaloids of this group is reported.
dc.format.extent13 p.
dc.format.mimetypeapplication/pdf
dc.identifier.idgrec568509
dc.identifier.issn0022-3263
dc.identifier.urihttps://hdl.handle.net/2445/159897
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.isformatofVersió postprint del document publicat a: https://doi.org/10.1021/jo0487101
dc.relation.ispartofJournal of Organic Chemistry, 2004, vol. 69, num. 25, p. 8681-8693
dc.relation.urihttps://doi.org/10.1021/jo0487101
dc.rights(c) American Chemical Society , 2004
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.sourceArticles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia)
dc.subject.classificationAlcaloides
dc.subject.classificationLactames
dc.subject.classificationSíntesi orgànica
dc.subject.otherAlkaloids
dc.subject.otherLactams
dc.subject.otherOrganic synthesis
dc.titleConjugate Addition to Phenylglycinol-Derived Unsaturated ä-Lactams. Enantioselective Synthesos of Uleine Alkaloids
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/acceptedVersion

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