title: 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.
authors: †Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, California 92697-2025, United States.
authors: Mary Elisabeth
authors: ME
authors: Daub
authors: ‡Department of Cell Biology and Neuroscience, University of California, Riverside, 900 University Avenue, Riverside, California 92521, United States.
authors: Jacques
authors: J
authors: Prudhomme
authors: ‡Department of Cell Biology and Neuroscience, University of California, Riverside, 900 University Avenue, Riverside, California 92521, United States.
authors: Karine
authors: K
authors: Le Roch
authors: †Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, California 92697-2025, United States.
authors: Christopher D
authors: CD
authors: Vanderwal
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002738:Chloroquine / Q000494:pharmacology; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004351:Drug Resistance / Q000187:drug effects; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D010963:Plasmodium falciparum / Q000187:drug effects*
chemical_list: D000962:Antimalarials; D004224:Diterpenes; C000604645:kalihinol B; D002738:Chloroquine