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Construction of Hexahydropyrido[3,2‐ c ]carbazole and Hexahydropyrrolo[3,2‐ c ]carbazole Skeletons for the Synthesis of Related Indole Alkaloids
Author(s) -
Hızlıateş Cevher Gündoğdu,
Gülle Sibel
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2467
Subject(s) - carbazole , chemistry , indole test , stereochemistry , combinatorial chemistry , organic chemistry
Synthesis of tetracyclic hexahydropyrido[3,2‐ c ]carbazoles ( 9a and 9b ) and hexahydropyrrolo[3,2‐ c ]carbazoles ( 13a and 13b ) structures was achieved via a new synthetic approach for the synthesis of related indole alkaloids such as deethylaspidospermidine and deethylibophyllidine. Hexahydropyrrolo[3,2‐ c ]carbazole structure was constructed for the first time starting from ethyl 4‐oxo‐cyclohexanecarboxylate in seven steps. Some tetrahydrocarbazole derivatives ( 4 , 5 , 6 , 7 , 11 , and 12 ) were also synthesized.