Synthesis and Potent Antimalarial Activity of Kalihinol B | Zendy

Mary Elisabeth Daub | Zendy; Jacques Prudhomme | Zendy; Karine G. Le Roch | Zendy; Christopher D. Vanderwal | Zendy

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Synthesis and Potent Antimalarial Activity of Kalihinol B

Author(s) -

Mary Elisabeth Daub,

Jacques Prudhomme,

Karine G. Le Roch,

Christopher D. Vanderwal

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.5b01152

Subject(s) - chemistry , plasmodium falciparum , potency , enantioselective synthesis , stereochemistry , tetrahydropyran , tetrahydrofuran , antimalarial agent , chloroquine , combinatorial chemistry , pharmacology , malaria , in vitro , biochemistry , organic chemistry , catalysis , ring (chemistry) , immunology , medicine , solvent , biology

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.

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