Diastereoselective synthesis of beta-ether derivatives of artemisinin, an antimalarial drug: the effect of nitrile on stereoselectivity
Title | Diastereoselective synthesis of beta-ether derivatives of artemisinin, an antimalarial drug: the effect of nitrile on stereoselectivity |
Publication Type | Journal Article |
Year of Publication | 2016 |
Authors | Chand, HR, Bhattacharya, AK |
Journal | Asian Journal of Organic Chemistry |
Volume | 5 |
Issue | 2 |
Pagination | 201-206 |
Date Published | FEB |
ISSN | 2193-5807 |
Keywords | antimalarials, 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. |
DOI | 10.1002/ajoc.201500415 |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 3.275 |