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

GÜNDOĞDU HIZLIATEŞ C., GÜLLE S.

Journal of Heterocyclic Chemistry, vol.53, no.5, pp.1584-1588, 2016 (SCI-Expanded, Scopus) identifier

  • Publication Type: Article / Article
  • Volume: 53 Issue: 5
  • Publication Date: 2016
  • Doi Number: 10.1002/jhet.2467
  • Journal Name: Journal of Heterocyclic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1584-1588
  • Manisa Celal Bayar University Affiliated: Yes

Abstract

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.