Highly Regioselective Protecting-Group-Free Synthesis of the Antimalarial Drug MMV693183

• DOI: 10.1021/acs.oprd.3c00353
• Publication Date: 2023-12-09T16:52:00Z
• Authors: Pankaj V. Khairnar; Sarah L. Aleshire; Ravi Kumar Ongolu; Limei Jin; Michael G. Laidlaw; Kai O. Donsbach; B. Frank Gupton; Ryan C. Nelson; Charles S. Shanahan
• Keywords: Protecting group

MMV693183 is a promising antimalarial drug candidate that works for uncomplicated malaria treatment and resistance management. Herein, we report an efficient highly regioselective synthesis of MMV693183. This novel synthetic method highlights three-step route with overall yield 46% from readily available starting materials. The key to the success lies in (1) utilizing subtle difference two amino groups material (S)-propane-1,2-diamine dihydrochloride without protection (2) identifying L-(+)-tartaric acid as counter organic salt formation, yielding desired regioisomer up 100:0. scalable protocol operates under mild conditions high chemo/regioselectivity, providing effective access