Synthesis and Potent Antimalarial Activity of Kalihinol B.
Daub, M. E.; Prudhomme, J.; Le Roch, K.; Vanderwal, C. D. Synthesis and Potent Antimalarial Activity of Kalihinol B. J. Am. Chem. Soc. 2015, 137, 4912-4915.
Of the 50+ kalihinane diterpenoids reported to date, only five had been tested for antimalarial activity, in spite of the fact that kalihinol A is the most potent among the members of the larger family of antimalarial isocyanoterpenes. We have validated a strategy designed to access many of the kalihinanes with a 12-step enantioselective synthesis of kalihinol B, the tetrahydrofuran isomer of kalihinol A (a tetrahydropyran). Kalihinol B shows similarly high potency against chloroquine-resistant Plasmodium falciparum.
Journal of the American Chemical Society