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Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/54342
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dc.contributor.CRUESPUNIVERSIDADE ESTADUAL DE CAMPINASpt_BR
dc.typeArtigopt_BR
dc.titleAn asymmetric substrate-controlled Morita–Baylis–Hillman reaction as approach for the synthesis of pyrrolizidinones and pyrrolizidinespt_BR
dc.contributor.authorLuna-Freire, Kristerson R.pt_BR
dc.contributor.authorScaramal, João Paulo S.pt_BR
dc.contributor.authorResende, Jackson A.L.C.pt_BR
dc.contributor.authorTormena, Cláudio F.pt_BR
dc.contributor.authorOliveira, Fábio L.pt_BR
dc.contributor.authorAparicio, Ricardopt_BR
dc.contributor.authorCoelho, Fernandopt_BR
unicamp.author.emailcoelho@iqm.unicamp.brpt_BR
unicamp.authorLuna-Freire, Kristerson R. Scaramal, Joao Paulo S. Coelho, Fernando Univ Estadual Campinas, Inst Chem, Lab Synth Nat Prod & Drugs, BR-13083970 Campinas, SP, Brazilpt_BR
unicamp.authorResende, Jackson A. L. C. Inst Quim UFF, Xray Diffract Lab, Niteroi, RJ, Brazilpt_BR
unicamp.authorTormena, Claudio F. Univ Estadual Campinas, Inst Chem, Lab Phys Organ Chem, BR-13083970 Campinas, SP, Brazilpt_BR
unicamp.authorOliveira, Fabio L. Aparicio, Ricardo Univ Estadual Campinas, Inst Chem, Lab Struct Biol & Crystallog, BR-13083970 Campinas, SP, Brazilpt_BR
dc.subjectMorita-Baylis-Hillmanpt_BR
dc.subjectHeterociclicospt_BR
dc.subjectPirrolizidinapt_BR
dc.subjectReação de Heckpt_BR
dc.subjectConfiguração absolutapt_BR
dc.subject.otherlanguageMorita-Baylis-Hillmanpt_BR
dc.subject.otherlanguageHeterocyclespt_BR
dc.subject.otherlanguagePyrrolizidinespt_BR
dc.subject.otherlanguageHeck reactionpt_BR
dc.subject.otherlanguageAbsolute configurationpt_BR
dc.subject.wosAlpha-glucosidase Inhibitorspt_BR
dc.subject.wosElectrospray-ionization Masspt_BR
dc.subject.wosStereoselective-synthesispt_BR
dc.subject.wosPolyhydroxylated Alkaloidspt_BR
dc.subject.wosGlycosidase Inhibitorspt_BR
dc.subject.wosIndolizidine Alkaloidspt_BR
dc.subject.wosMedicinal Chemistrypt_BR
dc.subject.wosBiological-activitypt_BR
dc.subject.wosNatural Occurrencept_BR
dc.subject.wosBeta-glucosidasept_BR
dc.description.abstractWe 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.pt
dc.description.abstractWe 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-aldehpt_BR
dc.relation.ispartofTetrahedronpt_BR
dc.publisher.cityOxfordpt_BR
dc.publisher.countryReino Unidopt_BR
dc.publisherElsevierpt_BR
dc.date.issued2014pt_BR
dc.date.monthofcirculationMaypt_BR
dc.identifier.citationTetrahedron. Pergamon-elsevier Science Ltd, v. 70, n. 20, n. 3319, n. 3326, 2014.pt_BR
dc.language.isoengpt_BR
dc.description.volume70pt_BR
dc.description.issuenumber20pt_BR
dc.description.firstpage3319pt_BR
dc.description.lastpage3326pt_BR
dc.rightsfechadopt_BR
dc.rights.licensehttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policypt_BR
dc.sourceWeb of Sciencept_BR
dc.identifier.issn0040-4020pt_BR
dc.identifier.eissn1464-5416pt_BR
dc.identifier.wosidWOS:000335873500016pt_BR
dc.identifier.doi10.1016/j.tet.2013.10.050pt_BR
dc.identifier.urlhttps://www.sciencedirect.com/science/article/pii/S0040402013015950pt_BR
dc.description.sponsorshipFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)pt_BR
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)pt_BR
dc.description.sponsorship1Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)pt_BR
dc.description.sponsorship1Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)pt_BR
dc.description.sponsorship1Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)pt_BR
dc.description.sponsordocumentnumberFAPESP [2011/20033-5, 2009/51602-5]pt
dc.date.available2014-07-30T13:48:34Z
dc.date.available2015-11-26T16:34:07Z-
dc.date.accessioned2014-07-30T13:48:34Z
dc.date.accessioned2015-11-26T16:34:07Z-
dc.description.provenanceMade available in DSpace on 2014-07-30T13:48:34Z (GMT). No. of bitstreams: 0 Previous issue date: 2014. Added 1 bitstream(s) on 2021-01-06T12:27:05Z : No. of bitstreams: 1 000335873500016.pdf: 1237938 bytes, checksum: 1b833be28cfe6493f305a635b758dd0e (MD5)en
dc.description.provenanceMade available in DSpace on 2015-11-26T16:34:07Z (GMT). No. of bitstreams: 0 Previous issue date: 2014en
dc.identifier.urihttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/54342
dc.identifier.urihttp://repositorio.unicamp.br/jspui/handle/REPOSIP/54342-
dc.subject.keywordStereoselectivitypt_BR
dc.type.formArtigopt_BR
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