title: Exploring chemical diversity of epoxyquinoid natural products: synthesis and biological activity of (-)-jesterone and related molecules.
abstract: Enantioselective syntheses of the potent antifungal agent (-)-jesterone, its hydroxy epimer, and a dimeric quinone epoxide derivative are reported. The synthesis involves diastereoselective epoxidation of a chiral quinone monoketal derivative and regio- and stereoselective reduction of a quinone epoxide intermediate.
authors.affiliation: Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA.
authors.forename: Y
authors.initials: Y
authors.lastname: Hu
authors.forename: C
authors.initials: C
authors.lastname: Li
authors.forename: B A
authors.initials: BA
authors.lastname: Kulkarni
authors.forename: G
authors.initials: G
authors.lastname: Strobel
authors.forename: E
authors.initials: E
authors.lastname: Lobkovsky
authors.forename: R M
authors.initials: RM
authors.lastname: Torczynski
authors.forename: J A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000935:Antifungal Agents; D004852:Epoxy Compounds; D007202:Indicators and Reagents; C431025:jesterone