title: Synthesis of Violaceic Acid and Related Compounds through Aryl Triazene.
abstract: MPC1001 is a potent anticancer natural product that contains a violaceic acid moiety. Herein we report the total synthesis of the natural product violaceic acid and its derivative. In this approach, a triazene-directed Ullman coupling proved to be highly effective. We converted the triazene to a hydroxy group by means of a palladium-catalyzed reaction. Treatment of the triazene with trifluoroacetic acid generated an arenediazonium ion that produced an aryl radical, leading to the protodediazoniation and a tricyclic product.
authors.affiliation: Department of Chemistry, University of Pittsburgh , 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, United States.
authors.forename: Shin
authors.identifier: 0000-0002-1087-5391
authors.initials: S
authors.lastname: Ando
authors.affiliation: Department of Chemistry, University of Pittsburgh , 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, United States.
authors.forename: James
authors.initials: J
authors.lastname: Burrows
authors.affiliation: Department of Chemistry, University of Pittsburgh , 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, United States.
authors.forename: Kazunori
authors.identifier: 0000-0001-8894-8485
authors.initials: K
authors.lastname: Koide
mesh_terms: D000143:Acids; D015394:Molecular Structure; D010165:Palladium; D014226:Triazenes / Q000737:chemistry*
chemical_list: D000143:Acids; D014226:Triazenes; D010165:Palladium