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A convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-ones

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dc.citation.titleOrganic and Biomolecular Chemistryes
dc.citation.volume14(9)es
dc.creatorSimonetti, Sebastián Osvaldo
dc.creatorLarghi, Enrique Leandro
dc.creatorKaufman, Teodoro Saúl
dc.date.accessioned2018-02-01T20:51:51Z
dc.date.available2018-02-01T20:51:51Z
dc.date.issued2016-01-26
dc.description5-Hydroxy-4-aryl-3,4-dihydro-1H-quinolin-2-ones are a small family of natural products isolated from fungal strains of Penicillium and Aspergillus. Most of its members, which are insecticides and anthelmintics, carry an isoprenoid C-6 side chain. The synthesis of a 6-propenyl-substituted advanced intermediate for the total synthesis of these natural products is presented in this paper. This was achieved through the stereoselective construction of a β,β-diarylacrylate derivative from 6-nitrosalicylaldehyde, using a Wittig olefination and a Heck–Matsuda arylation, followed by a selective Fe0-mediated reductive cyclization. Installation of the 6-propenyl side chain was performed by 5-O-allylation of the heterocycle, followed by Claisen rearrangement and conjugative migration of the allyl double bond, as the key steps. The Grubbs II-catalyzed olefin cross metathesis of the 6-allyl moiety with 2-methylbut-2-ene to afford a precursor of peniprequinolone is also reported.es
dc.description.filFil: Simonetti, Sebastián Osvaldo. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.es
dc.description.filFil: Larghi, Enrique Leandro. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.es
dc.description.filFil: Kaufman, Teodoro Saúl. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR-CONICET); Argentina.es
dc.description.sponsorshipConsejo Nacional de Investigaciones Científicas y Técnicas (CONICET), PIP no. 2012-0471es
dc.description.sponsorshipAgencia Nacional de Promoción Científica y Tecnológica (ANPCyT), PICTs no. 2011-0399 y 2014-0445es
dc.formatapplication/pdf
dc.format.extent2625 - 2636es
dc.identifier.issn1477-0520es
dc.identifier.urihttp://hdl.handle.net/2133/10489
dc.language.isoenges
dc.publisherRoyal Society of Chemistryes
dc.relation.ispartofseriesInformación complementaria: Selected spectra of intermediates and the final product. Ver el DOI: 10.1039/c5ob02680fes
dc.relation.ispartofseriesCorrección disponible: http://pubs.rsc.org/en/Content/ArticleLanding/2016/OB/C6OB90030E#!divAbstractes
dc.relation.publisherversionDOI: 10.1039/C5OB02680Fes
dc.relation.publisherversionhttp://pubs.rsc.org/en/content/articlelanding/2016/ob/c5ob02680f#!divAbstractes
dc.rightsopenAccesses
dc.rights.holderRoyal Society of Chemistryes
dc.rights.holderUniversidad Nacional de Rosarioes
dc.rights.holderSimonetti, Sebastián Osvaldoes
dc.rights.holderLarghi, Enrique Leandroes
dc.rights.holderKaufman, Teodoro Saúles
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/2.5/ar/*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/2.5/ar/*
dc.subjectBioactive 6-substituted 5-hydroxy4-aryl-1H-quinolin-2-oneses
dc.subjectNatural Productses
dc.subjectMetathesises
dc.subjectPrecursor of Peniprequinolonees
dc.titleA convenient approach to an advanced intermediate toward the naturally occurring, bioactive 6-substituted 5-hydroxy-4-aryl-1H-quinolin-2-oneses
dc.typearticle
dc.typeartículo
dc.typepublishedVersion
dc.type.collectionarticulo
dc.type.versionpublishedVersiones

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