| Abstract
| - In this paper, we report a simple route to accede to a new family of C-10 fluorinated derivatives ofartemisinin 7. We demonstrated that nucleophilic substitution of the allylic bromide 6 with alcohols canoccur at carbon 10 (compounds 7) under solvolytic conditions (SN‘/SN ratio, 87:13). Furthermore, usingthe particular properties of hexafluoroisopropanol (HFIP), we are able to increase the selectivity of thesubstitution. Primary alcohols are completely selective for allylic substitution. With amines as nucleophiles,selectivity of substitution is dependent on their nucleophilicity, but attack at carbon 16 was always favored.However, the SN‘/SN ratio could be slightly increased by adding HFIP, which is able to modulate theirnucleophilicity through hydrogen bonding. In preliminary in vitro assessments, these new compounds, 7,exhibited a satisfying activity against malaria.
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