Synthesis and Potent Antimalarial Activity of Kalihinol B

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 kali...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 137; no. 15; pp. 4912 - 4915
Main Authors: Daub, Mary Elisabeth, Prudhomme, Jacques, Le Roch, Karine, Vanderwal, Christopher D
Format: Journal Article
Language:English
Published: WASHINGTON American Chemical Society 22.04.2015
Amer Chemical Soc
Subjects:
Antimalarials - chemical synthesis
Antimalarials - chemistry
Antimalarials - pharmacology
Chemistry
Chemistry, Multidisciplinary
Chloroquine - pharmacology
Diterpenes - chemical synthesis
Diterpenes - chemistry
Diterpenes - pharmacology
Drug Resistance - drug effects
Molecular Structure
Parasitic Sensitivity Tests
Physical Sciences
Plasmodium falciparum - drug effects
Science & Technology
SPONGE
ETHER
NATURAL-PRODUCTS
DITERPENE ISONITRILES
RESISTANCE
ALDEHYDES
TERPENOIDS
MICHAEL ADDITION
ISSN:0002-7863, 1520-5126, 1520-5126
Online Access:Get full text
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Summary: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.
Bibliography:NIH RePORTER
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.5b01152