Synthesis and Potent Antimalarial Activity of Kalihinol B.

Authors

Mary Beth Daub, Furman UniversityFollow
Jacques Prudhomme, University of California, Riverside
Karine Le Roch, University of California, Riverside
Christopher D. Vanderwal, University of California, Irvine

ACS Citation

Daub, M. E.; Prudhomme, J.; Le Roch, K.; Vanderwal, C. D. Synthesis and Potent Antimalarial Activity of Kalihinol B. J. Am. Chem. Soc. 2015, 137, 4912-4915.

Version of Record

10.1021/jacs.5b01152

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.

Source Name

Journal of the American Chemical Society

Publication Date

3-27-2015

Volume

137

Issue

15

Page(s)

4912-4915

Document Type

Article

Citation Type

Article