Synthetic studies toward (−)-cleistenolide: highly stereoselective synthesis of new γ-lactone subunit

Registro completo de metadados
MetadadosDescriçãoIdioma
Autor(es): dc.creatorSartori, Suélen K.-
Autor(es): dc.creatorMiranda, Izabel L.-
Autor(es): dc.creatorMatos, Davi A. de-
Autor(es): dc.creatorKohlhoff, Markus-
Autor(es): dc.creatorDiaz, Marisa A. N.-
Autor(es): dc.creatorDiaz-Muñoz, Gaspar-
Data de aceite: dc.date.accessioned2026-02-09T11:16:32Z-
Data de disponibilização: dc.date.available2026-02-09T11:16:32Z-
Data de envio: dc.date.issued2022-02-10-
Data de envio: dc.date.issued2022-02-10-
Data de envio: dc.date.issued2021-04-
Fonte completa do material: dc.identifierhttps://repositorio.ufla.br/handle/1/49273-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/capes/1137375-
Descrição: dc.descriptionThis 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.-
Formato: dc.formatapplication/pdf-
Idioma: dc.languageen-
Publicador: dc.publisherSociedade Brasileira de Química-
Direitos: dc.rightsAttribution 4.0 International-
Direitos: dc.rightsAttribution 4.0 International-
Direitos: dc.rightsacesso aberto-
Direitos: dc.rightshttp://creativecommons.org/licenses/by/4.0/-
Direitos: dc.rightshttp://creativecommons.org/licenses/by/4.0/-
???dc.source???: dc.sourceJournal of the Brazilian Chemical Society-
Palavras-chave: dc.subject(−)-cleistenolide-
Palavras-chave: dc.subjectγ-lactone-
Palavras-chave: dc.subjectdiacetonide diol-
Palavras-chave: dc.subjectd-mannitol-
Título: dc.titleSynthetic studies toward (−)-cleistenolide: highly stereoselective synthesis of new γ-lactone subunit-
Tipo de arquivo: dc.typeArtigo-
Aparece nas coleções:Repositório Institucional da Universidade Federal de Lavras (RIUFLA)

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