Synthesis of antimalarial yingzhaosu A analogues by the peroxidation of dienes with Co(II)/O2/Et3SiH.
Co(II)-catalyzed peroxidation of dienes including (S)-limonene in the presence of molecular oxygen and triethylsilane provided in each case the corresponding 2,3-dioxabicyclo[3.3.1]nonane derivatives via the intramolecular cyclization of the unsaturated peroxy radical intermediates. The product composition was remarkably influenced by the structure of the dienes, the nature of the solvents, and the concentration of the substrates and the catalyst. Some of the yingzhaosu A analogues obtained in this study showed notable antimalarial activities in vitro.
Tokuyasu
Takahiro
T
Department of Materials Chemistry & Frontier Research Center, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Kunikawa
Shigeki
S
Abe
Manabu
M
Masuyama
Araki
A
Nojima
Masatomo
M
Kim
Hye-Sook
HS
Begum
Khurshida
K
Wataya
Yusuke
Y
D000466:Alkadienes / Q000737:chemistry; D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis*; D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D003035:Cobalt; D051379:Mice; D010084:Oxidation-Reduction; D010100:Oxygen; D010545:Peroxides / Q000138:chemical synthesis*; D010963:Plasmodium falciparum / Q000187:drug effects; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D012821:Silanes; D013329:Structure-Activity Relationship
D000466:Alkadienes; D000962:Antimalarials; D010545:Peroxides; D012717:Sesquiterpenes; D012821:Silanes; D003035:Cobalt; C467230:yingzhaosu A; D010100:Oxygen