title: New methods for the synthesis of naphthyl amines; application to the synthesis of dihydrosanguinarine, sanguinarine, oxysanguinarine and (±)-maclekarpines B and C.
abstract: A new method for preparing naphthyl amines from 1,5 unsaturated dicarbonyl precursors is described; the utility of this new method was proven in the syntheses of several natural products, all containing the benzo[c]phenanthridine core and enabled by a radical promoted cyclisation of the naphthyl amine products formed in the key cyclisation.
authors.affiliation: Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk.
authors.forename: Matthew R
authors.initials: MR
authors.lastname: Tatton
authors.forename: Iain
authors.initials: I
authors.lastname: Simpson
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Donohoe
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D052117:Benzodioxoles / Q000138:chemical synthesis*; D053119:Benzophenanthridines / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis; D007546:Isoquinolines / Q000138:chemical synthesis; D010617:Phenanthridines / Q000138:chemical synthesis
chemical_list: D000588:Amines; D052117:Benzodioxoles; D053119:Benzophenanthridines; D001688:Biological Products; D007546:Isoquinolines; D010617:Phenanthridines; C511014:oxysanguinarine; C501843:dihydrosanguinarine; C005705:sanguinarine