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| Title
| - Preparation of 10-Trifluoromethyl Artemether and Artesunate.Influence of Hexafluoropropan-2-ol on Substitution Reaction
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| Abstract
| - To prepare 10-trifluoromethyl analogues of important antimalarials such as artemether andartesunate, the substitution reaction of the 10-trifluoromethyl hemiketal 6 and bromide 4 derivedfrom artemisinin was investigated. While 6 appeared to be unreactive under various conditions,bromide 4 could easily undergo substitution with methanol under electrophilic assistance ornoncatalyzed conditions. Optimization of the reaction revealed the role of CH2Cl2 as solvent toavoid the competitive elimination process and the crucial influence of hexafluoro-2-propanol (HFIP)in increasing the rate and the stereoselectivity of the substitution reaction (de >98%). The efficiencyof this reaction was exemplified with various alcohols and carboxylates (yield up to 89%).
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