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Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis
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The azocino[4,3-b]indole system, tricyclic substructure of the indole alkaloids apparicine and ervaticine, is efficiently assembled by ring-closing metathesis of 2-allyl-3-(allylaminomethyl)indoles. The metathesis sites are introduced into the indole nucleus by reductive amination of a 3-formyl derivative with allylamine, followed by a-lithiation with subsequent electrophilic trapping with acrolein.
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BENNASAR FÈLIX, M. Lluïsa, et al. Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis. Tetrahedron. 2007. Vol. 63, num. 4, pags. 861-866. ISSN 0040-4020. [consulted: 11 of October of 2026]. Available at: https://hdl.handle.net/2445/160425