title: Total Synthesis of the Oxopolyene Macrolide (-)-Marinisporolide C.
abstract: 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 the 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 bonds and six stereogenic centers. Additionally, a very efficient Julia-Kocieński reaction was used to install a C22-C23 double bond, and the macrocyclic ring was closed using an intramolecular Horner-Wadsworth-Emmons olefination.
authors.affiliation: Institute of Chemistry, University of Campinas , 13083-970, C.P. 6154, Campinas, SP, Brasil.
authors.forename: Luiz C
authors.initials: LC
authors.lastname: Dias
authors.affiliation: Institute of Chemistry, University of Campinas , 13083-970, C.P. 6154, Campinas, SP, Brasil.
authors.forename: Emílio C
authors.initials: EC
authors.lastname: de Lucca
mesh_terms: D039903:Actinobacteria / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D018942:Macrolides; C000606843:marinisporolide C; C116609:3-hydroxybutanal