Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids

G Bar, A F Parsons, C B Thomas

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Tricyclic quinoline alkaloids, including araliopsine 2, can be prepared in 'one-pot' by reaction of 4-hydroxy-1-methyl-2(1H)quinoline 5 or 2,4-quinolinediol 31 with manganese(III) acetate in the presence of a variety of electron-rich alkenes. The reaction mechanism involves an initial intermolecular radical addition reaction followed by radical oxidation and cyclisation steps. Both angular and linear tricyclic alkaloids can be formed and the regioselectivity of the cyclisation is shown to depend on whether alkyl or aryl groups are attached to the alkene. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)4719-4728
Number of pages10
Issue number22
Publication statusPublished - 28 May 2001


  • alkaloids
  • manganese and compounds
  • quinolines
  • radicals and radical reactions

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