Biomimetic Construction of the Hydroquinoline Ring System. Diastereodivergent Enantioselective Synthesis of 2,5-Disubstituted cis-Decahydroquinolines

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dc.contributor.authorAmat Tusón, Mercedes
dc.contributor.authorFabregat, Robert
dc.contributor.authorGriera Farres, Rosa
dc.contributor.authorFlorindo, Pedro
dc.contributor.authorMolins i Grau, Elies
dc.contributor.authorBosch Cartes, Joan
dc.date.accessioned2019-01-17T12:49:45Z
dc.date.available2019-01-17T12:49:45Z
dc.date.issued2010-03-31
dc.date.updated2019-01-17T12:49:46Z
dc.description.abstractThe straightforward enantioselective construction of the hydroquinoline ring system from 1,5-polycarbonyl derivatives, using (R)-phenyglycinol as a chiral latent form of ammonia, is reported. The process mimics the key steps believed to occur in nature in the biosynthesis of amphibian decahydroquinoline alkaloids. Diastereodivergent routes to enantiopure cis-2,5-disubstituted decahydroquinolines, including the alkaloid pumiliotoxin C (cis-195A), are developed.
dc.format.extent9 p.
dc.format.mimetypeapplication/pdf
dc.identifier.idgrec579354
dc.identifier.issn0022-3263
dc.identifier.urihttps://hdl.handle.net/2445/127382
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.isformatofVersió postprint del document publicat a: https://doi.org/10.1021/jo1005894
dc.relation.ispartofJournal of Organic Chemistry, 2010, vol. 75, num. 11, p. 3797-3805
dc.relation.urihttps://doi.org/10.1021/jo1005894
dc.rights(c) American Chemical Society , 2010
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.sourceArticles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
dc.subject.classificationBiosíntesi
dc.subject.classificationBiomimètica
dc.subject.classificationSíntesi asimètrica
dc.subject.classificationSíntesi orgànica
dc.subject.otherBiosynthesis
dc.subject.otherBiomimetics
dc.subject.otherAsymmetric synthesis
dc.subject.otherOrganic synthesis
dc.titleBiomimetic Construction of the Hydroquinoline Ring System. Diastereodivergent Enantioselective Synthesis of 2,5-Disubstituted cis-Decahydroquinolines
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/acceptedVersion

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