TY - JOUR
T1 - Synthesis of 1,5-diaryl-2-fluoro-6,7-dioxabicyclo[3.2.2]nonanes with high antimalarial activity utilizing photoinduced electron-transfer oxygenation reactions
AU - Kamata, Masaki
AU - Maeda, Rie
AU - Hayakawa, Jun
AU - Kim, Hye Sook
N1 - Funding Information:
We gratefully acknowledge financial support provided by The Uchida Energy Science Promotion Foundation (No.33, 2018). We also thank Professor Hiroshi Ikeda, Dr. Takuya Ogaki, and Mr. Shun Irii (Department of Chemistry, Graduate School of Engineering, Osaka Prefecture University) for their helpful assistance and comments.
Publisher Copyright:
© 2022 Elsevier Ltd
PY - 2022/4/27
Y1 - 2022/4/27
N2 - 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.
AB - 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.
KW - Antimalarial activity
KW - Fluorinated bicyclic peroxide
KW - Photoinduced electron-transfer (PET) oxygenation
KW - Triphenylpyrylium salt
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U2 - 10.1016/j.tetlet.2022.153752
DO - 10.1016/j.tetlet.2022.153752
M3 - Article
AN - SCOPUS:85127351209
SN - 0040-4039
VL - 96
JO - Tetrahedron Letters
JF - Tetrahedron Letters
M1 - 153752
ER -