title: Palladium-Catalyzed Ullmann Cross-Coupling/Tandem Reductive Cyclization Route to Key Members of the Uleine Alkaloid Family.
abstract: The trisubstituted cyclohexenone 12, generated through a palladium-catalyzed Ullmann cross-coupling reaction between o-iodonitrobenzene and a 4,5-trans-disubstituted 2-iodo-2-cyclohexen-1-one, engaged in a tandem reductive cyclization process upon exposure to hydrogen gas in the presence of Raney cobalt. As a result, the 1,5-methanoazocino[4,3-b]indole 13 was obtained and this could be readily elaborated to the racemic modifications of the alkaloids uleine, dasycarpidone, noruleine, and nordasycarpidone (1-4, respectively).
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 / Q000138:chemical synthesis* / Q000737:chemistry; D001392:Azocines / Q000138:chemical synthesis* / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: C581627:1,5-methanoazocino(4,3-b)indole; C000610806:2-iodo-2-cyclohexen-1-one; D000470:Alkaloids; D001392:Azocines; D001952:Bridged-Ring Compounds; D003512:Cyclohexanones; D007211:Indoles; D009578:Nitrobenzenes; C000610805:o-iodonitrobenzene; C428545:uleine; D003035:Cobalt; D010165:Palladium