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Synfacts 2011(9): 0935-0935  
DOI: 10.1055/s-0030-1260911
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Mefloquine Hydrochloride

Contributor(s): Philip Kocienski
J. D. Knight, S. J. Sauer, D. M. Coltart*
Duke University, Durham, USA
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

Racemic mefloquine hydrochloride (Lariam®) is used for the treatment and prevention of malaria. The (+)-enantiomer is slightly more active than the (-)-enantiomer and it displays reduced neurotoxicity. The key step in the synthesis depicted is the asymmetric Darzens reaction (A → C) involving a hydrazone chiral auxiliary.