Construction of Hexahydropyrido[3,2‐c]carbazole and Hexahydropyrrolo[3,2‐c]carbazole Skeletons for the Synthesis of Related Indole Alkaloids

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‐...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 53; no. 5; pp. 1584 - 1588
Main Authors Hizliates, Cevher Gundogdu, Gulle, Sibel
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.09.2016
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
(+/-)-DEETHYLIBOPHYLLIDINE
IBOPHYLLIDINE SKELETON
VINCA ALKALOIDS
ANNULATION
PATHWAY
DIELS-ALDER REACTION
CORE STRUCTURE
ASPIDOSPERMA ALKALOIDS
STRYCHNOS ALKALOIDS
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Summary: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.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.2467