title: A biomimetic strategy to access the silybins: total synthesis of (-)-isosilybin A.
abstract: We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products.
authors.affiliation: Dept. of Chemistry, Dept. of Pharmacology, Center for Molecular Innovation and Drug Discovery, Northwestern University , 2145 Sheridan Road, Evanston, Illinois 60208, United States.
authors.forename: Benjamin R
authors.initials: BR
authors.lastname: McDonald
authors.forename: Antoinette E
authors.initials: AE
authors.lastname: Nibbs
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002599:Chalcone / Q000737:chemistry; D003500:Cyclization; D020944:Silybum marianum / Q000737:chemistry; D015394:Molecular Structure; D012838:Silymarin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D012838:Silymarin; D002599:Chalcone; C523198:isosilybin A