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Access to enantiopure 4-substituted 1,5-aminoalcohols from phenylglycinol-derived δ-lactams: synthesis of Haliclona alkaloiods

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dc.contributor.authorAmat Tusón, Mercedes
dc.contributor.authorGuignard, Guillaume Michel Pablo
dc.contributor.authorLlor Brunés, Núria
dc.contributor.authorBosch Cartes, Joan
dc.date.accessioned2016-05-30T17:39:01Z
dc.date.available2016-05-30T17:39:01Z
dc.date.issued2014-03-21
dc.date.updated2016-05-30T17:39:06Z
dc.description.abstractLiNH2BH3-promoted reductive opening of 8-substituted phenylglycinol-derived oxazolopiperidone lactams leads to enantiopure 4-substituted-5-aminopentanols, which are used as starting building blocks in the synthesis of the Haliclona alkaloids haliclorensin C, haliclorensin, and halitulin (formal). The starting lactams are easily accessible by a cyclocondensation reaction of (R)-phenylglycinol with racemic γ-subtituted δ-oxoesters, in a process that involves a dynamic kinetic resolution.
dc.format.extent11 p.
dc.format.mimetypeapplication/pdf
dc.identifier.idgrec643221
dc.identifier.issn0022-3263
dc.identifier.pmid24555853
dc.identifier.urihttps://hdl.handle.net/2445/99053
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.isformatofVersió postprint del document publicat a: http://dx.doi.org/10.1021/jo5002627
dc.relation.ispartofJournal of Organic Chemistry, 2014, vol. 79, num. 6, p. 2792-2802
dc.relation.urihttp://dx.doi.org/10.1021/jo5002627
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.classificationSíntesi orgànica
dc.subject.classificationAlcaloides
dc.subject.classificationLactames
dc.subject.classificationCompostos heterocíclics
dc.subject.otherOrganic synthesis
dc.subject.otherAlkaloids
dc.subject.otherLactams
dc.subject.otherHeterocyclic compounds
dc.titleAccess to enantiopure 4-substituted 1,5-aminoalcohols from phenylglycinol-derived δ-lactams: synthesis of Haliclona alkaloiods
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/acceptedVersion

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