title: Total Synthesis of (-)-Marinisporolide C.
abstract: 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 Stille cross-coupling reaction to assemble the polyene, and an intramolecular 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.
authors.affiliation: Institute of Chemistry, University of Campinas , C.P. 6154, Campinas, SP 13083-970, Brazil.
authors.forename: Luiz C
authors.identifier: 0000-0003-0628-9928
authors.initials: LC
authors.lastname: Dias
authors.affiliation: Institute of Chemistry, University of Campinas , C.P. 6154, Campinas, SP 13083-970, Brazil.
authors.forename: Emilio C
authors.initials: EC
authors.lastname: de Lucca
mesh_terms: D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; C000606843:marinisporolide C