Studies on the Synthesis of Heterocyclic Compounds. Part 832. A Simple and Efficient Synthesis of Apomitomycin Derivatives; a Potential Intermediate for Mitomycin Synthesis

DOI: 10.1039/P19800001607

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1607 - 1613 (1980)

Update date:2022-08-05

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Authors:

Kametani, Tetsuji

Kigawa, Yoshio

Nemoto, Hideo

Ihara, Masataka

Fukumoto, Keiichiro

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Article abstract of DOI:10.1039/P19800001607

Condensation of pyrrolidine-2-thione (21) with methyl α-bromo-(2-bromo-4,5-dimethoxyphenyl)acetate (15) gave methyl (Z)-α-(2-bromo-4,5-dimethoxyphenyl)-α-pyrrolidin-2-ylideneacetate (25) in high yield.Several other methyl (Z)-α-aryl-α-<3-acetoxy-4-(N-ethoxycarbonyl-N-methylamino)pyrrolidin-2-ylidene>acetates (26)-(31) were also synthesised in good yields from reaction of the corresponding phenylacetates (15), (12), and (13) with trans-3-acetoxy-4-(N-ethoxycarbonyl-N-methylamino)pyrrolidine-2-thione (20).Treatment of compounds (25)-(31) with sodium hydride and copper(I) bromide in dimethylformamide afforded methyl 2,3-dihydro-6,7-dimethoxy-1H-pyrrolo<1,2-a>indole-9-carboxylate (34) and the methyl (+/-)-trans-1-acetoxy-2-(N-ethoxycarbonyl-N-methylamino)-2,3-dihydro-1H-pyrrolo<1,2-a>indole-9-carboxylates (35)-(37) in good yields.Methyl (+/-)-trans-1-acethoxy-2-(N-ethoxycarbonyl-N-methylamino)-2,3-dihydro-7-methoxy-6-methyl-1H-pyrrolo<1,2-a>indole-9-carboxylate (36) was converted into the 5,8-quinone (3), via the 8-nitro-compound (38).

Full text of DOI:10.1039/P19800001607

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