Concise Total Syntheses of Pyrido[4,3‐ b ]carbazole Alkaloids Using Copper‐Mediated 6π‐Electrocyclization | Zendy

Itoh Tomoki | Zendy; Abe Takumi | Zendy; Choshi Tominari | Zendy; Nishiyama Takashi | Zendy; Yanada Reiko | Zendy; Ishikura Minoru | Zendy

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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

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.

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