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Campo DC | Valor | Idioma |
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dc.creator | Sartori, Suélen K. | - |
dc.creator | Miranda, Izabel L. | - |
dc.creator | Matos, Davi A. de | - |
dc.creator | Kohlhoff, Markus | - |
dc.creator | Diaz, Marisa A. N. | - |
dc.creator | Diaz-Muñoz, Gaspar | - |
dc.date.accessioned | 2022-02-11T16:47:14Z | - |
dc.date.available | 2022-02-11T16:47:14Z | - |
dc.date.issued | 2021-04 | - |
dc.identifier.citation | SARTORI, 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.uri | http://repositorio.ufla.br/jspui/handle/1/49273 | - |
dc.description.abstract | This 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.language | en_US | pt_BR |
dc.publisher | Sociedade Brasileira de Química | pt_BR |
dc.rights | Attribution 4.0 International | * |
dc.rights | acesso aberto | pt_BR |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | * |
dc.source | Journal of the Brazilian Chemical Society | pt_BR |
dc.subject | (−)-cleistenolide | pt_BR |
dc.subject | γ-lactone | pt_BR |
dc.subject | diacetonide diol | pt_BR |
dc.subject | d-mannitol | pt_BR |
dc.title | Synthetic studies toward (−)-cleistenolide: highly stereoselective synthesis of new γ-lactone subunit | pt_BR |
dc.type | Artigo | pt_BR |
Aparece nas coleções: | DQI - Artigos publicados em periódicos |
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