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dc.creatorSartori, Suélen K.-
dc.creatorMiranda, Izabel L.-
dc.creatorMatos, Davi A. de-
dc.creatorKohlhoff, Markus-
dc.creatorDiaz, Marisa A. N.-
dc.creatorDiaz-Muñoz, Gaspar-
dc.date.accessioned2022-02-11T16:47:14Z-
dc.date.available2022-02-11T16:47:14Z-
dc.date.issued2021-04-
dc.identifier.citationSARTORI, S. K. et al. Synthetic studies toward (−)-cleistenolide: highly stereoselective synthesis of new γ-lactone subunits. Journal of the Brazilian Chemical Society, [S.l.], v. 32, n. 4, Apr. 2021.pt_BR
dc.identifier.urihttp://repositorio.ufla.br/jspui/handle/1/49273-
dc.description.abstractThis study describes the stereoselective synthesis of two new γ-lactones in 6 and 3 steps and 19 and 32% yield, respectively, directed toward the total synthesis of the natural product (−)-cleistenolide. The starting material was an enantiomerically pure diacetonide diol, derived from d-mannitol with the required stereocenters for (−)-cleistenolide synthesis. γ-Lactone syntheses were based on highly selective protection and deprotection of hydroxyls from d-mannitol. The formation of γ-lactone rings was the culmination of this approach, made possible by a Horner-Wadsworth-Emmons Z-olefination between diacetal aldehyde and ethyl 2-(bis(o-tolyloxy)phosphoryl)acetate to produce an unsaturated ester. The Z-isomer ester was highly favored in relation to the E-isomer (Z/E ratio of 94:6), allowing the formation of the γ-lactone ring under acid catalysis. This strategy precluded the use of chiral auxiliaries or catalysts for the control of stereocenters in the novel γ-lactones.pt_BR
dc.languageen_USpt_BR
dc.publisherSociedade Brasileira de Químicapt_BR
dc.rightsAttribution 4.0 International*
dc.rightsacesso abertopt_BR
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.sourceJournal of the Brazilian Chemical Societypt_BR
dc.subject(−)-cleistenolidept_BR
dc.subjectγ-lactonept_BR
dc.subjectdiacetonide diolpt_BR
dc.subjectd-mannitolpt_BR
dc.titleSynthetic studies toward (−)-cleistenolide: highly stereoselective synthesis of new γ-lactone subunitpt_BR
dc.typeArtigopt_BR
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