TY - JOUR
T1 - Palladium-Catalyzed Ullmann Cross-Coupling/Tandem Reductive Cyclization Route to Key Members of the Uleine Alkaloid Family
AU - Tang, Fei
AU - Banwell, Martin G.
AU - Willis, Anthony C.
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/4/15
Y1 - 2016/4/15
N2 - 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).
AB - 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).
UR - http://www.scopus.com/inward/record.url?scp=84963787344&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.6b00240
DO - 10.1021/acs.joc.6b00240
M3 - Article
SN - 0022-3263
VL - 81
SP - 2950
EP - 2957
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 7
ER -