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Paper | Regular issue | Vol 83, No. 5, 2011, pp.1111-1119
Published online, 23rd March, 2011
DOI: 10.3987/COM-11-12167
Simple Synthesis of Pratosine and Hippadine by Intramolecular Palladium-Catalyzed Cyclization and Decarboxylation

Hideaki Umemoto, Masashi Dohshita, Hiromi Hamamoto, and Yasuyoshi Miki*

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan


The palladium-catalyzed cyclization of dimethyl 1-(2-bromo-4,5-dimethoxybenzyl)indole-2,3-dicarboxylate in the presence of tetrakis(triphenylphosphine)palladium(0) and potassium acetate in hot 1,4-dioxane produced the 7H-pyrrolo[3,2,1-de]phenanthridine derivative, which was converted to pratosine by hydrolysis and decarboxylation. In a similar manner, hippadine was also prepared.