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Total Synthesis of Marinoquinoline A Using a Palladium(0)‐Catalyzed Ullmann Cross‐Coupling Reaction
Author(s) -
Ma Xinghua,
Vo Yen,
Banwell Martin G.,
Willis Anthony C.
Publication year - 2012
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201200037
Subject(s) - chemistry , palladium , yield (engineering) , catalysis , methanol , ullmann reaction , natural product , magnesium , coupling reaction , coupling (piping) , combinatorial chemistry , organic chemistry , metallurgy , materials science
The title natural product, 1 , has been synthesized. The pivotal steps are a Pd 0 ‐catalyzed Ullmann cross‐coupling of the 3‐iodopyrrole‐2‐carboxaldehyde 13 with o ‐bromonitrobenzene ( 14 ), conversion of the resulting 3‐arylpyrrole 15 into methylketone 17 , and reductive cyclization of 17 by using magnesium in methanol to give target 1 in 85 % yield.