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Synthesis of the ABC ring of calyciphylline A-type alkaloids by a stereocontrolled aldol cyclization: Formal synthesis of (±)-Himalensine A

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dc.contributor.authorMarquès, Clàudia
dc.contributor.authorDiaba, Faïza
dc.contributor.authorGómez-Bengoa, Enrique
dc.contributor.authorBonjoch, Josep
dc.date.accessioned2024-10-25T13:35:42Z
dc.date.available2024-10-25T13:35:42Z
dc.date.issued2022-07-21
dc.date.updated2024-10-25T13:35:42Z
dc.description.abstractA synthetic approach to a functionalized ABC-tricyclic framework of calyciphilline A-type alkaloids, a building block toward this class of alkaloids, is reported. The key synthetic steps involve a radical cyclization to form the hydroindole system and piperidine ring closure through a stereocontrolled aldol cyclization. The resulting alcohol allows the methyl group to be installed in the bowl-shaped azatricyclic structure; this crucial reaction takes place with configuration retention. The synthesis of azatricyclic compound I constitutes a formal synthesis of himalensine A.
dc.format.extent7 p.
dc.format.mimetypeapplication/pdf
dc.identifier.idgrec724469
dc.identifier.issn0022-3263
dc.identifier.urihttps://hdl.handle.net/2445/216055
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.isformatofReproducció del document publicat a: https://doi.org/10.1021/acs.joc.2c01171
dc.relation.ispartofJournal of Organic Chemistry, 2022, vol. 87, num.15, p. 10516-10522
dc.relation.urihttps://doi.org/10.1021/acs.joc.2c01171
dc.rightscc-by (c) Marquès et al., 2022
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/es/*
dc.sourceArticles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
dc.subject.classificationReacció aldòlica
dc.subject.classificationCromatografia
dc.subject.classificationMescles
dc.subject.otherAldol reaction
dc.subject.otherChromatography
dc.subject.otherMixtures
dc.titleSynthesis of the ABC ring of calyciphylline A-type alkaloids by a stereocontrolled aldol cyclization: Formal synthesis of (±)-Himalensine A
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/publishedVersion

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