title: Biomimetic Approach to the Catalytic Enantioselective Synthesis of Flavonoids.
abstract: Herein is reported the direct asymmetric addition of phenol nucleophiles to benzopyrylium salts as a means to produce enantioenriched flavonoid-like compounds. This enantioselective C-C bond construction was achieved through a chiral anion phase-transfer strategy that mimics the proposed biosynthesis of this structurally diverse set of natural products. The utility of this methodology was demonstrated in enantioselective synthesis of a 2,8-dioxabicyclo[3.3.1]nonane and a 2,4-diarylbenzopyran.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Zhenyu
authors.initials: Z
authors.lastname: Yang
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Ying
authors.initials: Y
authors.lastname: He
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
mesh_terms: D000838:Anions; D001688:Biological Products / Q000737:chemistry*; D032701:Biomimetics; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D002851:Chromatography, High Pressure Liquid; D015195:Drug Design; D004583:Electrons; D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000838:Anions; D001688:Biological Products; D005419:Flavonoids; D010636:Phenols; D002244:Carbon