Total Synthesis of the Oxopolyene Macrolide (-)-Marinisporolide C

Autor(es)

Dias, Luiz C. ^[1] ; de Lucca, Jr., Emilio C. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC LETTERS; v. 17, n. 24, p. 6278-6281, DEC 18 2015.
• Citações Web of Science: 8

Resumo

The first total synthesis of (-)-marinisporolide C was performed in 25 steps (longest linear sequence) and an overall yield. of 1%. Due to the high degree of convergence and robustness, the C9-C35 fragment that corresponds to polyol portion was obtained in gram quantity: Highlights, of this synthesis include five highly stereoselective aldol reactions responsible for the construction Of five C-C bond's and six stereogenic Centers: Additionally, a very efficient Julia-Kocienski reaction was used to install a C22-C23 double bond, and the macrocyclic was closed using an intramolecular Horner-Wadsworth-Emmons olefination. (AU)

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