1,5-Diaryl-2-fluoro-6,7-dioxabicyclo[3.2.2]nonanes were synthesized from corresponding 3-fluoro-2,6-diarylhepta-1,6-dienes utilizing 2,4,6-triphenylpyrylium salt (TPPX: X = BF4, ClO4)-sensitized photoinduced electron-transfer (PET) oxygenation reactions, and their in-vitro antimalarial activity was evaluated. Results showed that these fluorinated bicyclic peroxides had higher antimalarial activity than their nonfluorinated parent bicyclic peroxides. In addition, it was shown that PET oxygenation reactions, particularly TPPX-biphenyl-cosensitized PET oxygenation reactions, are an efficient method for the construction of a C–O–O–C structure during the synthesis of fluorinated antimalarial bicyclic peroxides.
- Antimalarial activity
- Fluorinated bicyclic peroxide
- Photoinduced electron-transfer (PET) oxygenation
- Triphenylpyrylium salt
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry