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

Fei Tang | Zendy; Martin G. Banwell | Zendy; Anthony C. Willis | Zendy

Open Access

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

Author(s) -

Fei Tang,

Martin G. Banwell,

Anthony C. Willis

Publication year - 2016

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.6b00240

Subject(s) - chemistry , tandem , palladium , catalysis , alkaloid , ullmann reaction , coupling (piping) , combinatorial chemistry , key (lock) , organic chemistry , stereochemistry , materials science , composite material , mechanical engineering , ecology , engineering , biology

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).

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