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Stereoselective total synthesis of the putative structure of nitraraine

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dc.contributor.authorArioli, Federica
dc.contributor.authorPérez Bosch, Maria
dc.contributor.authorSubrizi, Fabiana
dc.contributor.authorLlor Brunés, Núria
dc.contributor.authorBosch Cartes, Joan
dc.contributor.authorAmat Tusón, Mercedes
dc.date.accessioned2016-06-03T14:44:09Z
dc.date.available2016-06-03T14:44:09Z
dc.date.issued2014-08-15
dc.date.updated2016-06-03T14:44:14Z
dc.description.abstractAfter the structure originally proposed for nitraraine was shown to be incorrect by total synthesis, the alternative structure 5 was recently suggested for the alkaloid on biosynthetic grounds and by comparison with the (1)H NMR data of tangutorine. The unambiguous synthesis of 5 is reported from tryptophanol and ketodiester 6, via oxazoloquinolone lactam 7. However, the melting point and (1)H NMR data of 5 did not match those reported for the natural product.
dc.format.extent6 p.
dc.format.mimetypeapplication/pdf
dc.identifier.idgrec643223
dc.identifier.issn0022-3263
dc.identifier.pmid25019615
dc.identifier.urihttps://hdl.handle.net/2445/99223
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.isformatofVersió postprint del document publicat a: http://dx.doi.org/10.1021/jo5013543
dc.relation.ispartofJournal of Organic Chemistry, 2014, vol. 79, num. 16, p. 7740-7745
dc.relation.urihttp://dx.doi.org/10.1021/jo5013543
dc.rights(c) American Chemical Society , 2014
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.sourceArticles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
dc.subject.classificationAlcaloides
dc.subject.classificationSíntesi orgànica
dc.subject.classificationLactames
dc.subject.classificationCompostos heterocíclics
dc.subject.classificationTriptòfan
dc.subject.otherAlkaloids
dc.subject.otherOrganic synthesis
dc.subject.otherLactams
dc.subject.otherHeterocyclic compounds
dc.subject.otherTryptophan
dc.titleStereoselective total synthesis of the putative structure of nitraraine
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/acceptedVersion

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