Expeditious Synthesis of the Marine Natural Products Prepolycitrin A and Polycitrins A and B through Heck Arylations

dc.creatorCanto, K
dc.creatorRibeiro, RD
dc.creatorBiajoli, AFP
dc.creatorCorreia, CRD
dc.date2013
dc.dateDEC
dc.date2014-07-30T17:32:03Z
dc.date2015-11-26T17:46:03Z
dc.date2014-07-30T17:32:03Z
dc.date2015-11-26T17:46:03Z
dc.date.accessioned2018-03-29T00:28:32Z
dc.date.available2018-03-29T00:28:32Z
dc.identifierEuropean Journal Of Organic Chemistry. Wiley-v C H Verlag Gmbh, v. 2013, n. 35, n. 8004, n. 8013, 2013.
dc.identifier1434-193X
dc.identifier1099-0690
dc.identifierWOS:000327775800021
dc.identifier10.1002/ejoc.201301108
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/66329
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/66329
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1288374
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionNew, efficient protocols for the syntheses of the marine natural products prepolycitrin A as well as polycitrins A and B were developed by employing the Heck-Matsuda arylation of maleic anhydride or dimethyl fumarate with aryldiazonium tetrafluoroborates. Both symmetrical and unsymmetrical 3,4-diarylmaleic anhydrides were easily and effectively prepared. Efficient bromination reactions that employed tribromoisocyanuric acid provided access to the polycitrin family of compounds. Under microwave irradiation in the presence of tyramine, the corresponding maleimides were obtained in high yields from the brominated 3,4-diarylmaleic anhydrides. This methodology provided for the concise synthesis of prepolycitrin A and the total syntheses of the marine alkaloids polycitrins A and B in overall yields of 37 and 47% from maleic anhydride and dimethyl fumarate, respectively.
dc.description2013
dc.description35
dc.description8004
dc.description8013
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionFAPESP [2011/23832-6]
dc.languageen
dc.publisherWiley-v C H Verlag Gmbh
dc.publisherWeinheim
dc.publisherAlemanha
dc.relationEuropean Journal Of Organic Chemistry
dc.relationEur. J. Org. Chem.
dc.rightsfechado
dc.rightshttp://olabout.wiley.com/WileyCDA/Section/id-406071.html
dc.sourceWeb of Science
dc.subjectTotal synthesis
dc.subjectHeterocycles
dc.subjectAlkaloids
dc.subjectHeck reaction
dc.subjectPalladium
dc.subjectCross-coupling Reactions
dc.subjectAryl Chlorides
dc.subjectMaleic Anhydrides
dc.subjectDiazonium Salts
dc.subjectC-c
dc.subjectTribromoisocyanuric Acid
dc.subjectPalladium Catalysts
dc.subjectAromatic Rings
dc.subjectAlkaloids
dc.subjectPurpurone
dc.titleExpeditious Synthesis of the Marine Natural Products Prepolycitrin A and Polycitrins A and B through Heck Arylations
dc.typeArtículos de revistas


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