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Straightforward Synthesis of Isoellipticine by Palladium‐Catalysed Coupling Reactions
Author(s) -
Naciuk Fabrício F.,
Castro Joaquim A. M.,
Serikava Bruno K.,
Miranda Paulo C. M. L.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702602
Subject(s) - palladium , intramolecular force , yield (engineering) , chemistry , catalysis , ring (chemistry) , combinatorial chemistry , nucleus , quinone , oxidative coupling of methane , coupling reaction , photochemistry , organic chemistry , materials science , metallurgy , biology , microbiology and biotechnology
Our novel synthetic route to isoellipticine featured palladium‐catalyzed intramolecular reactions for the construction of the B ring of the pyridocarbazole nucleus. The adequate palladium‐catalyzed reaction depended upon the oxidation conditions that were applied in order to prepare the immediate synthetic precursor. When CAN was used to make the quinone intermediate, an oxidative cyclization through a double C−H bond activation was applied. Conversely, when the oxidation condition involved TCCA as oxidant, a direct C−H arylation was employed. Both approaches showed similar efficiencies in order to construct the pyridocarbazole nucleus. Isoellipticine was prepared in only 5 steps with a 21%–23% overall yield.