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Enantioselective synthesis of lepadins A D from a phenylglycinol-derived hydroquinolone lactam

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dc.contributor.authorAmat Tusón, Mercedes
dc.contributor.authorPinto, Alexandre
dc.contributor.authorGriera Farres, Rosa
dc.contributor.authorBosch Cartes, Joan
dc.date.accessioned2017-03-07T13:11:15Z
dc.date.available2017-03-07T13:11:15Z
dc.date.issued2015-07-21
dc.date.updated2017-03-07T13:11:15Z
dc.description.abstractThe marine alkaloids (-)-lepadins A-C and (+)-lepadin D, belonging to two diastereoisomeric series, were synthesized from an (R)-phenylglycinol-derived tricyclic lactam via a common cis-decahydroquinoline intermediate. Crucial aspects of the synthesis are the stereochemical control in the assembly of the cis-decahydroquinoline platform, in the introduction of the C2 methyl and C3 hydroxy substituents, and in the generation of the C5 stereocenter.
dc.format.extent5 p.
dc.format.mimetypeapplication/pdf
dc.identifier.idgrec655588
dc.identifier.issn0947-6539
dc.identifier.pmid26202059
dc.identifier.urihttps://hdl.handle.net/2445/108026
dc.language.isoeng
dc.publisherWiley-VCH
dc.relation.isformatofVersió postprint del document publicat a: https://doi.org/10.1002/chem.201501909
dc.relation.ispartofChemistry-A European Journal, 2015, vol. 21, num. 36, p. 12804-12808
dc.relation.urihttps://doi.org/10.1002/chem.201501909
dc.rights(c) Wiley-VCH, 2015
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.sourceArticles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
dc.subject.classificationAlcaloides
dc.subject.classificationLactames
dc.subject.classificationCompostos heterocíclics
dc.subject.classificationSíntesi asimètrica
dc.subject.otherAlkaloids
dc.subject.otherLactams
dc.subject.otherHeterocyclic compounds
dc.subject.otherAsymmetric synthesis
dc.titleEnantioselective synthesis of lepadins A D from a phenylglycinol-derived hydroquinolone lactam
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/acceptedVersion

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