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A short route to functionalized imidazo[4,5-c]carbazoles. Synthesis of the first example of the imidazo[4,5-c]β-carboline ring system

✍ Scribed by Said Achab; Khalid Diker; Pierre Potier

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 127 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01915-3

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✦ Synopsis

A new synthetic route to functionalized imidazo[4,5-c]carbazoles (4) via intramolecular electrocyclization of indolo-1,3,5-hexatriene system (3a) is described. Thermally induced ring-closure of 2-ethylcarboxylate-(4-amino-5-imidazolyl)-3-indole (3d) led to the previously unknown imidazo[4,5-c]b-carboline ring system (5). These heterocycles were efficiently converted into analogs of both the marine cytotoxic agents grossularines-1 and -2 (1) and the antimicrobial alkaloid eudistomin U (2).

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