Total Synthesis of (-)-Marinisporolide C

Autor(es)

Dias, Luiz C. ; de Lucca, Emilio C.

• Tipo de documento: Artigo Científico
• Fonte: Journal of Organic Chemistry; v. 82, n. 6, p. 3019-3045, MAR 17 2017.
• Citações Web of Science: 11

Resumo

The first total synthesis of (-)-marinisporolide C is described, which establishes unequivocally the relative and absolute configuration of this oxopolyene macrolide. Key features of this synthesis include a series of highly stereoselective aldol reactions followed by directed reductions to build the polyol domain, a Stile cross-coupling reaction to assemble the polyene, and an infra molecular Horner-Wadsworth-Emmons olefination to forge the macrocyclic ring. Despite the initial approach to marinisporolide A using a Yamaguchi macrolactonization reaction that was unsuccessful due to steric hindrance of the oxygen at the C33 position, we were able to prepare a known derivative of marinisporolide A and consequently confirm its stereochemical assignment. (AU)

• Processo FAPESP: 12/02230-0 - Síntese total de produtos bioativos: testes biológicos e design de novos análogos estruturais
• Beneficiário: Luiz Carlos Dias
• Linha de fomento: Auxílio à Pesquisa - Regular
• Processo FAPESP: 11/06721-6 - Síntese total do marinisporolideo a
• Beneficiário: Emílio Carlos de Lucca Júnior
• Linha de fomento: Bolsas no Brasil - Doutorado
• Processo FAPESP: 13/07600-3 - CIBFar - Centro de Inovação em Biodiversidade e Fármacos
• Beneficiário: Glaucius Oliva
• Linha de fomento: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs