title: Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: application to the preparation of natural flavones and isoflavones.
abstract: A Lewis acid-triggered zincation allows the regioselective metalation of various chromones and quinolones. In the absence of MgCl(2), a C(3) zincation is observed, whereas in the presence of MgCl(2) or a related Lewis acid, C(2) zincation occurs. Applications to a natural flavone, isoflavone, and quinolone are shown.
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus F, 81377 Munich, Germany.
authors.forename: Lydia
authors.initials: L
authors.lastname: Klier
authors.forename: Tomke
authors.initials: T
authors.lastname: Bresser
authors.forename: Tobias A
authors.initials: TA
authors.lastname: Nigst
authors.forename: Konstantin
authors.initials: K
authors.lastname: Karaghiosoff
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis; D002867:Chromones / Q000138:chemical synthesis / Q000737:chemistry*; D047309:Flavones / Q000138:chemical synthesis*; D007529:Isoflavones / Q000138:chemical synthesis*; D058116:Lewis Acids / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
chemical_list: D001688:Biological Products; D002867:Chromones; D047309:Flavones; D007529:Isoflavones; D058116:Lewis Acids; D015363:Quinolones; D015032:Zinc