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First Synthesis of the Antimalarial Naphthylisoquinoline Alkaloid Dioncophylline C, and Its Unnatural Anti-Hiv Dimer, Jozimine C

  1. Author:
    Bringmann, G.
    Holenz, J.
    Weirich, R.
    Rubenacker, M.
    Funke, C.
    Boyd, M. R.
    Gulakowski, R. J.
    Francois, G.
    1. Year: 1998
  2. Journal: Tetrahedron
    1. 54
    2. 3-4
    3. Pages: 497-512
  4. Type of Article: Article
  1. Abstract:

    The first total synthesis of dioncophylline C, a new antimalarial lead structure, is described. For the directed construction of the stereogenic biaryl axis, the 'lactone methodology' is applied, despite the lack of a 'bridgehead oxygen' function in the target molecule. Furthermore, the novel dimer of dioncophylline C, 'jozimine C, is prepared, by oxidative phenolic coupling of the protected natural monomer. Jozimine C displays good antimalarial activity (Plasmodium falciparum; IC50 = 0.445 mu g/ml), and, in particular, represents the first unnatural dimer of a naphthylisoquinoline alkaloid with a high anti-HIV activity (HIV-1; EC50 = 27 mu g/ml). (C) 1997 Elsevier Science Ltd. All rights reserved. [References: 26]

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