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Paper | Regular issue | Vol 65, No. 11, 2005, pp.2693-2703
Published online, 26th August, 2005
DOI: 10.3987/COM-05-10522
Synthesis of 3-Methoxyellipticine and Ellipticine by Friedel-Crafts Reaction of Indole-2,3-dicarboxylic Anhydride and Selective Demethylation

Yasuyoshi Miki,* Yoshiyuki Aoki, Yasuhiko Tsuzaki, Misako Umemoto, and Hajime Hibino

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

Abstract

Reaction of 1-benzylindole-2,3-dicarboxylic anhydride with 2,4,6-trimethoxypyridine in the presence of a Lewis acid gave 1-benzyl-3-(2,4,6-trimethoxynicotinoyl)indole-2-carboxylic acid as the sole product in high yield, which could be changed to 1-benzyl-3-(2,4,6-trimethoxynicotinoyl)indole. 1 Benzyl-3 (2,4,6-trimethoxynicotinoyl)indole was converted to 3 methoxy¬ellipticine and ellipticine by selective demethylation and triflation of the methoxy group.