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Communication | Regular issue | Vol 12, No. 5, 1979, pp.685-689
Published online, 1st January, 1970
DOI: 10.3987/R-1979-05-0685
The Synthesis of a Potential Intermediate to Apomitomycin

Tetsuji Kametani,* Yoshio Kigawa, Hideo Nemoto, Masataka Ihara, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Condensation of methyl α-bromo-(2-bromo-4,5-dimethoxyphenyl)acetate (10) with 2-thiopyrrolidone (11) and with trans-3-acetoxy-4-(N-ethoxycarbonyl-N-methylamino)-2-thiopyrrolidone (14) gave in high yields methyl (Z)-α-(2-bromo-4,5-dimethoxyphenyl)-α-pyrrolidine-2-ylideneacetate (12), and methyl α-[3-acetoxy-4-(N-ethoxycarbonyl-N-methylamino)pyrrolidine-2-ylidene]acetates (15) and (16), respectively. Treatment of compounds 12 and 15 or 16 with sodium hydride and cuprous bromide in dimethylformamide afforded, again in good yields, methyl 6,7-dimethoxy-1H-pyrrolo[1,2-a]indole-9-carboxylate (13) and methyl trans-1-acetoxy-2-[N-ethoxycarbonyl-N-methylamino]-6,7-dimethoxy-1H-pyrrolo[1,2-a]indole-9-carboxylate (17), respectively.