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Regioselective Synthesis of Ellipticine
Author(s) -
Ho TseLok,
Hsieh ShengYing
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690001
Subject(s) - chemistry , regioselectivity , carbazole , indene , yield (engineering) , halogenation , alkaloid , suzuki reaction , stereochemistry , organic chemistry , combinatorial chemistry , palladium , catalysis , materials science , metallurgy
An eight‐step synthesis of the tetracyclic pyridocarbazole alkaloid ellipticine (= 5,11‐dimethyl‐6 H ‐pyrido[4,3‐ b ]carbazole; 1a ) in an overall yield of 13% is reported, starting from 4,7‐dimethyl‐1 H ‐indene. Key steps were iodination, Suzuki coupling, reductive cyclization, DDQ oxidation, and heterocyclization under loss of H 2 O.