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Octadehydromichellamine, a structural analog of the anti-HIV michellamines without centrochirality

  1. Author:
    Bringmann, G.
    Wenzel, M.
    Kelly, T. R.
    Boyd, M. R.
    Gulakowski, R. J.
    Kaminsky, R.

  2. Author Address

    Bringmann G Univ Wurzburg, Inst Organ Chem Hubland D-97074 Wurzburg Germany Univ Wurzburg, Inst Organ Chem D-97074 Wurzburg Germany Boston Coll, Dept Chem, Eugene F Merkert Chem Ctr Chestnut Hill, MA 02467 USA NCI, Lab Drug Discovery Res & Dev Frederick, MD 21702 USA Swiss Trop Inst CH-4002 Basel Switzerland
    1. Year: 1999
  2. Journal: Tetrahedron
    1. 55
    2. 6
    3. Pages: 1731-1740
  4. Type of Article: Article
  1. Abstract:

    The synthesis of octadehydromichellamine (4), as the fully dehydrogenated structural analog of the naturally occurring michellamines (1), is described. This derivative is the first michellamine-type quateraryl without centrochirality and thus constitutes a distinctly simplified structural michellamine analog. Key step of the total synthesis is the twofold coupling of a bis-O-triflate activated central binaphthalene building block 9 with 2 eq. of the isoquinoline boronic acid 8, to give the quateraryl 11, whose deprotection delivers the target molecule 4, in an apparently stereochemically pure form. Octadehydromichellamine (4) shows a good order of anti-HIV activity and, compared with natural michellamines, enhanced antimalarial activity against Plasmodium falciparum. (C) 1999 Elsevier Science Ltd. All rights reserved. [References: 25]

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