title: Synthesis of antimalarial yingzhaosu A analogues by the peroxidation of dienes with Co(II)/O2/Et3SiH.
abstract: 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.
authors.affiliation: Department of Materials Chemistry & Frontier Research Center, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
authors.forename: Takahiro
authors.initials: T
authors.lastname: Tokuyasu
authors.forename: Shigeki
authors.initials: S
authors.lastname: Kunikawa
authors.forename: Manabu
authors.initials: M
authors.lastname: Abe
authors.forename: Araki
authors.initials: A
authors.lastname: Masuyama
authors.forename: Masatomo
authors.initials: M
authors.lastname: Nojima
authors.forename: Hye-Sook
authors.initials: HS
authors.lastname: Kim
authors.forename: Khurshida
authors.initials: K
authors.lastname: Begum
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Wataya
mesh_terms: 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
chemical_list: D000466:Alkadienes; D000962:Antimalarials; D010545:Peroxides; D012717:Sesquiterpenes; D012821:Silanes; D003035:Cobalt; C467230:yingzhaosu A; D010100:Oxygen