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Trapped in misbelief for almost 40 years: Selective synthesis of the four stereoisomers of mefloquine.

MPS-Authors
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Schützenmeister,  N.
Department of NMR Based Structural Biology, MPI for biophysical chemistry, Max Planck Society;

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Reinscheid,  U. M.
Department of NMR Based Structural Biology, MPI for biophysical chemistry, Max Planck Society;

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Griesinger,  C.
Department of NMR Based Structural Biology, MPI for biophysical chemistry, Max Planck Society;

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Leonov,  A.
Department of NMR Based Structural Biology, MPI for biophysical chemistry, Max Planck Society;

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Citation

Schützenmeister, N., Müller, M., Reinscheid, U. M., Griesinger, C., & Leonov, A. (2013). Trapped in misbelief for almost 40 years: Selective synthesis of the four stereoisomers of mefloquine. Chemistry, 19(51), 17584-17588. doi:10.1002/chem.201303403.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0015-0E93-F
Abstract
Here we report the synthesis of all four stereoisomers of mefloquine. Mefloquine (Lariam) is an important anti-malaria drug that is applied as a racemate of the erythro form. However, the (-)-isomer induces psychosis, while the (+)-enantiomer does not have this undesired side effect. There are six syntheses of which five lead to the wrong enantiomer without the authors of these syntheses noting that they had synthesized the wrong compound. At the same time physical chemistry investigations had assigned the absolute configuration correctly and the last enantioselective synthesis that took these results into account delivered the correct absolute configuration. Since various synthetic approaches failed to provide the correct stereoisomers in previous syntheses, we submit here a synthetic approach with a domino Sonogashira-6-electrocyclisation as key step that confirmed synthetically the correct absolute configuration of all four isomers.