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The Absolute Configuration of (+)- and (−)-erythro-Mefloquine

Authors

  • Dr. Michael Müller,

    1. Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)
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  • M. Sc. Claudia M. Orben,

    1. Institut für Anorganische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany)
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  • Dr. Nina Schützenmeister,

    1. Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)
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  • Dipl.-Chem. Manuel Schmidt,

    1. Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)
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  • Dr. Andrei Leonov,

    1. Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)
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  • Prof. Dr. Uwe M. Reinscheid,

    Corresponding author
    1. Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)
    • Uwe M. Reinscheid, Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)

      Birger Dittrich, Institut für Anorganische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany)

      Christian Griesinger, Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)

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  • Dr. Birger Dittrich,

    Corresponding author
    1. Institut für Anorganische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany)
    • Uwe M. Reinscheid, Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)

      Birger Dittrich, Institut für Anorganische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany)

      Christian Griesinger, Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)

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  • Prof. Dr. Christian Griesinger

    Corresponding author
    1. Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)
    • Uwe M. Reinscheid, Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)

      Birger Dittrich, Institut für Anorganische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 4, 37077 Göttingen (Germany)

      Christian Griesinger, Max-Planck-Institut für Biophysikalische Chemie, Department of NMR-Based Structural Biology, Am Fassberg 11, 37077 Göttingen (Germany)

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  • Support by the MPG (to C.G.) and the DFG (FOR 934 to C.G. and U.M.R.) is acknowledged. We thank Prof. L. F. Tietze for continuous support.

Abstract

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The controversy over the absolute configuration of (+)-erythro-mefloquine, the less psychosis-causing enantiomer of the anti-malarial drug Lariam, has been resolved by Mosher ester crystallization. The configuration determined previously by physical methods (see scheme) is correct, whereas the configuration determined by three enantioselective syntheses is wrong.

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