Tang, FeiBanwell, MartinWillis, Anthony2021-01-072021-01-070022-3263http://hdl.handle.net/1885/219212The 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).We thank the Australian Research Council and the Instiute of Advanced Studies for financial support. F.T. is the grateful recipient of a CSC Ph.D. Scholarship provided by the Government of the People’s Republic of China.application/pdfen-AU© 2016 American Chemical Societyalkaloidsazocinesbridged-ring compoundscatalysiscobaltcyclizationcyclohexanonesindolesmolecular structurenitrobenzenespalladium2016-04-0110.1021/acs.joc.6b00240