title: A Raney Cobalt Mediated Reductive Cyclization Route to the Uleine Alkaloid Gilbertine.
abstract: Reductive cyclization of the 2,4,5-trisubstituted cyclohexenone 16 using dihydogen in the presence of Raney cobalt afforded compound 17 (60%) that could be elaborated over a further five steps, including one involving a cationic cyclization process, into the racemic modification of the unusual uleine alkaloid gilbertine. Single-crystal X-ray analyses of compounds (±)-1, 16, and a derivative of 17 are reported.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Fei
authors.initials: F
authors.lastname: Tang
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D003035:Cobalt / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D013058:Mass Spectrometry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D066244:Proton Magnetic Resonance Spectroscopy
chemical_list: D000470:Alkaloids; D001952:Bridged-Ring Compounds; C428545:uleine; D003035:Cobalt