An asymmetric substrate-controlled Morita-Baylis-Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines

dc.creatorLuna-Freire, KR
dc.creatorScaramal, JPS
dc.creatorResende, JALC
dc.creatorTormena, CF
dc.creatorOliveira, FL
dc.creatorAparicio, R
dc.creatorCoelho, F
dc.date2014
dc.dateMAY 20
dc.date2014-07-30T13:48:34Z
dc.date2015-11-26T16:34:07Z
dc.date2014-07-30T13:48:34Z
dc.date2015-11-26T16:34:07Z
dc.date.accessioned2018-03-28T23:16:16Z
dc.date.available2018-03-28T23:16:16Z
dc.identifierTetrahedron. Pergamon-elsevier Science Ltd, v. 70, n. 20, n. 3319, n. 3326, 2014.
dc.identifier0040-4020
dc.identifierWOS:000335873500016
dc.identifier10.1016/j.tet.2013.10.050
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/54342
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/54342
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1271097
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionWe describe herein an approach to the total synthesis of functionalized pyrrolizidinones and pyrrolizidines. The synthetic sequence is based on a highly stereoselective substrate-controlled Morita-Baylis-Hillman (MBH) reaction between a chiral amino-aldehyde and methyl acrylate. The selectivity attained in this reaction was controlled by the presence of a hydroxyl group adequately placed in the structure of the amino-aldehyde used as the nucleophilic component of the MBH reaction. The MBH adducts were used as substrate for an efficient total synthesis of pyrrolizidinones and pyrrolizidines in good overall yield. (C) 2013 Elsevier Ltd. All rights reserved.
dc.description70
dc.description20
dc.description3319
dc.description3326
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionFAPESP [2011/20033-5, 2009/51602-5]
dc.languageen
dc.publisherPergamon-elsevier Science Ltd
dc.publisherOxford
dc.publisherInglaterra
dc.relationTetrahedron
dc.relationTetrahedron
dc.rightsfechado
dc.rightshttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dc.sourceWeb of Science
dc.subjectMorita-Baylis-Hillman
dc.subjectHeterocycles
dc.subjectPyrrolizidines
dc.subjectHeck reaction
dc.subjectStereoselectivity
dc.subjectAbsolute configuration
dc.subjectAlpha-glucosidase Inhibitors
dc.subjectElectrospray-ionization Mass
dc.subjectStereoselective-synthesis
dc.subjectPolyhydroxylated Alkaloids
dc.subjectGlycosidase Inhibitors
dc.subjectIndolizidine Alkaloids
dc.subjectMedicinal Chemistry
dc.subjectBiological-activity
dc.subjectNatural Occurrence
dc.subjectBeta-glucosidase
dc.titleAn asymmetric substrate-controlled Morita-Baylis-Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidines
dc.typeArtículos de revistas


Este ítem pertenece a la siguiente institución