title: Stereoselective Total Synthesis of (-)-Depudecin.
abstract: The total synthesis of the natural product depudecin, an antiangiogenic microbial polyketide with inhibitory activity against histone deacetylases, is reported. Characterized by a highly oxidized 11-carbon chain containing two epoxides conjugated through a trans-disubstituted olefin, its total synthesis was efficiently accomplished by a novel asymmetric methodology of epoxide formation based on a new class of chiral sulfonium salts, allowing for the construction of the oxirane rings in an efficient and stereoselective fashion.
authors.affiliation: Department of Organic Chemistry, Faculty of Sciences, University of Málaga , Campus de Teatinos s/n, 29071 Málaga, Spain.
authors.forename: Cristina
authors.initials: C
authors.lastname: García-Ruiz
authors.affiliation: Department of Organic Chemistry, Faculty of Sciences, University of Málaga , Campus de Teatinos s/n, 29071 Málaga, Spain.
authors.forename: Iván
authors.initials: I
authors.lastname: Cheng-Sánchez
authors.affiliation: Department of Organic Chemistry, Faculty of Sciences, University of Málaga , Campus de Teatinos s/n, 29071 Málaga, Spain.
authors.forename: Francisco
authors.initials: F
authors.lastname: Sarabia
mesh_terms: D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes; D000528:Alternaria / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D000475:Alkenes; D001688:Biological Products; D004852:Epoxy Compounds; D005233:Fatty Alcohols; C072251:depudecin