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Title: | Synthetic studies toward (−)-cleistenolide: highly stereoselective synthesis of new γ-lactone subunit |
Keywords: | (−)-cleistenolide γ-lactone diacetonide diol d-mannitol |
Issue Date: | Apr-2021 |
Publisher: | Sociedade Brasileira de Química |
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. |
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. |
URI: | http://repositorio.ufla.br/jspui/handle/1/49273 |
Appears in Collections: | DQI - Artigos publicados em periódicos |
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File | Description | Size | Format | |
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ARTIGO_Synthetic studies toward.pdf | 301,77 kB | Adobe PDF | View/Open |
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