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Synthesis and potent antimalarial activity of kalihinol B.


ABSTRACT: 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.

SUBMITTER: Daub ME 

PROVIDER: S-EPMC4415034 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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Synthesis and potent antimalarial activity of kalihinol B.

Daub Mary Elisabeth ME   Prudhomme Jacques J   Le Roch Karine K   Vanderwal Christopher D CD  

Journal of the American Chemical Society 20150409 15


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  ...[more]

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