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Concise Total Syntheses of Pyrido[4,3‐ b ]carbazole Alkaloids Using Copper‐Mediated 6π‐Electrocyclization
Author(s) -
Itoh Tomoki,
Abe Takumi,
Choshi Tominari,
Nishiyama Takashi,
Yanada Reiko,
Ishikura Minoru
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600246
Subject(s) - chemistry , carbazole , tandem , electrocyclic reaction , alkaloid , stereochemistry , cascade reaction , total synthesis , combinatorial chemistry , catalysis , organic chemistry , bicyclic molecule , materials science , composite material
Abstract Concise syntheses of 9‐methoxyellipticine, 3,4‐dihydroellipticine (µ‐alkaloid D), 1,2,3,4‐tetrahydroellipticine, 2‐methyl‐1,2,3,4‐tetrahydroellipticine, olivacine, 3,4‐dihydroolivacine, (±)‐guatambuine, and (±)‐janetine were developed starting from hexatriene intermediates readily obtained by Pd‐catalyzed tandem cyclization/cross‐coupling reaction of indolylborates. The route enables the facile construction of pyrido[4,3‐ b ]carbazoles by Cu‐catalyzed 6π‐electrocyclization and subsequent transformation of the pyridocarbazole intermediates into pyrido[4,3‐ b ]carbazole alkaloids.