Synthesis and potent antimalarial activity of kalihinol B.
- Author(s): Daub, Mary Elisabeth
- Prudhomme, Jacques
- Le Roch, Karine
- Vanderwal, Christopher D
- et al.
Published Web Locationhttps://doi.org/10.1021/jacs.5b01152
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.