Diastereoselective synthesis of beta-ether derivatives of artemisinin, an antimalarial drug: the effect of nitrile on stereoselectivity

TitleDiastereoselective synthesis of beta-ether derivatives of artemisinin, an antimalarial drug: the effect of nitrile on stereoselectivity
Publication TypeJournal Article
Year of Publication2016
AuthorsChand, HR, Bhattacharya, AK
JournalAsian Journal of Organic Chemistry
Volume5
Issue2
Pagination201-206
Date PublishedFEB
ISSN2193-5807
Keywordsantimalarials, arteethers, artemisinin, nitriles, trichloroacetimidates
Abstract

Malaria is a life-threatening disease affecting a major portion of the world's population with considerable loss of human life. Artemisinin, isolated from Artemisia annua, its oil- and water-soluble derivatives, and other known antimalarials are recommended for artemisinin combination therapy by the World Health Organization. We have established a method for the stereoselective synthesis of beta-ether derivatives of dihydroartemisinin in high yield and high diastereoselectivity. The reaction either in acetonitrile or dichloromethane/trichloroacetonitrile (6:1) mixtures at 0 degrees C or room temperature, respectively, furnished the antimalarial drugs artemether 3 or arteether 4 in high yield with a high diastereomeric ratio. The effect the nitrile has on the yield and stereoselectivity is mechanistically explained.

DOI10.1002/ajoc.201500415
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)3.275
Divison category: 
Organic Chemistry