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Concise Synthesis and Antimalarial Activity of All Four Mefloquine Stereoisomers Using a Highly Enantioselective Catalytic Borylative Alkene Isomerization


  • This research was generously funded by the Natural Sciences and Engineering Research Council (NSERC) of Canada, and the University of Alberta. The authors thank Stéphanie Lessard for advice and discussions. We also thank the Medicines for Malaria Venture (Dr. Xavier Ding) for their support in providing and coordinating the biological tests.


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The pluses and minuses of mefloquine: A highly enantioselective catalytic borylative isomerization/aldehyde allylboration method for the stereoselective synthesis of the antimalarial drug mefloquine was optimized, thus leading to an efficient synthesis of all four mefloquine stereoisomers and analogues (see scheme). The absolute configuration of these potent compounds was determined for the first time by using chemical synthesis.