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Palladium-Catalyzed Ullmann Cross-Coupling/Tandem Reductive Cyclization Route to Key Members of the Uleine Alkaloid Family

Tang, Fei; Banwell, Martin; Willis, Anthony


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...[Show more]

CollectionsANU Research Publications
Date published: 2016-04-01
Type: Journal article
Source: The Journal of organic chemistry
DOI: 10.1021/acs.joc.6b00240
Access Rights: Open Access


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