| Author | Sartori, Suélen Karine | |
| Author | Miranda, Izabel L. | |
| Author | Matos, Davi A. de | |
| Author | Kohlhoff, Markus | |
| Author | Diaz, Marisa A. N. | |
| Author | Diaz-Muñoz, Gaspar | |
| Access date | 2022-02-10T18:11:58Z | |
| Available date | 2022-02-10T18:11:58Z | |
| Document date | 2021 | |
| Citation | SARTORI, Suélen Karine et al. Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits. Journal of the Brazilian Chemical Society, v. 32, n. 4, p. 757-766, Apr. 2021. | pt_BR |
| ISSN | 0103-5053 | pt_BR |
| URI | https://www.arca.fiocruz.br/handle/icict/51142 | |
| Language | eng | pt_BR |
| Publisher | Sociedade Brasileira de Química | pt_BR |
| Rights | open access | pt_BR |
| Title | Synthetic Studies toward (-)-Cleistenolide: Highly Stereoselective Synthesis of New gamma-Lactone Subunits | pt_BR |
| Type | Article | pt_BR |
| DOI | 10.21577/0103-5053.20200227 | |
| 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 |
| Affilliation | Universidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, Brazil. | pt_BR |
| Affilliation | Universidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, Brazil. | pt_BR |
| Affilliation | Universidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, Brazil. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto René Rachou. Química de Produtos Naturais. Belo Horizonte, MG, Brazil. | pt_BR |
| Affilliation | Universidade Federal de Viçosa. Departamento de Bioquímica e Biologia Molecula. Viçosa, MG, Brazil. | pt_BR |
| Affilliation | Universidade Federal de Minas Gerais. Departamento de Química. Belo Horizonte, MG, Brazil. | pt_BR |
| Subject | Highly Stereoselective Synthesis | pt_BR |
| Subject | Diacetonide diol | pt_BR |
