title: Synthetic studies of 7-oxygenated aporphine alkaloids: preparation of (-)-oliveroline, (-)-nornuciferidine, and derivatives.
abstract: 7-Oxygenated aporphines 1-6 possessing anti-configurations have previously been reported. In order to explore their bioactivities, a synthesis was established by utilizing a diastereoselective reductive acid-mediated cyclization followed by palladium-catalyzed ortho-arylations. Moderate XPhos precatalyst loading (10 mol %) and short reaction times (30 min) were sufficient to mediate the arylations. Alkaloids 1-5 were successfully prepared, while (-)-artabonatine A was revised to syn-isomer 30. Consequently, (-)-artabonatine E likely also has a syn-configuration (31).
authors.affiliation: Department of Chemistry and ‡Department of Pharmacological and Pharmaceutical Sciences, University of Houston , Science and Research Building 2, Rm 549A, Houston, Texas 77204, United States.
authors.forename: Angela F
authors.initials: AF
authors.lastname: Ku
authors.forename: Gregory D
authors.initials: GD
authors.lastname: Cuny
mesh_terms: D000470:Alkaloids; D001060:Aporphines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007536:Isomerism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010165:Palladium; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001060:Aporphines; D011166:Porphyrins; C438398:artabonatine E; C000600750:nornuciferidine; D010165:Palladium; C014140:oliveroline