Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 127, Issue 4-5, Pages 637-642Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2005.12.013
Keywords
gem-difluoroolefin; artemisinin; malaria; mimic effect; carbohydrate lactone
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Exo gem-difluoromethylene-artemisinins (8) has been designed to mimic artemisinin. The classical Wittig olefination reaction applied to artemisinin failed. An alternative reaction involving the generation of an alpha-CF3 carbanion, from the corresponding bromide 6, allowed the access to the target compound 8, and could also be exemplified in sugar series. The replacement of the carbonyl function by a difluoroethylene moiety resulted in a better antimalarial activity. (C) 2006 Elsevier B.V. All rights reserved.
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