1-Benzylindole-2,3-dicarboxylic anhydride (1) was reacted with 2,4,6-trimethoxypyridine in the presence of titanium(IV) chloride to give 3-(2,4,6-trimethoxynicotinoyl)indole-2-carboxylic acid (2) as the sole product in high yield, which could be converted to olivacine.
Alkaloids U 0600Synthesis of 3-Methoxyolivacine and Olivacine by Friedel-Crafts Reaction of Indole-2,3-dicarboxylic Anhydride with 2,4,6-Trimethoxypyridine. -Key step in the synthesis of olivacine (VIII) is the regioselective Friedel-Crafts reaction of compound (I) and trimethoxypyridine (II). (VIII) is reported to possess strong anticancer activity. -(MIKI*, Y.; TSUZAKI, Y.; HIBINO, H.; AOKI, Y.; Synlett 2004, 12, 2206-2208; Fac. Pharm. Sci., Kinki Univ., Higashi-Osaka, Osaka 577, Japan; Eng.) -C. Oppel
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