364594-20-7Relevant academic research and scientific papers
Synthesis of antimalarial yingzhaosu A analogues by the peroxidation of dienes with Co(II)/O2/Et3SiH
Tokuyasu, Takahiro,Kunikawa, Shigeki,Abe, Manabu,Masuyama, Araki,Nojima, Masatomo,Kim, Hye-Sook,Begum, Khurshida,Wataya, Yusuke
, p. 7361 - 7367 (2007/10/03)
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.
Yingzhaosu A analogues: Synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis and determination of anti-malarial activity
Tokuyasu, Takahiro,Masuyama, Araki,Nojima, Masatomo,McCullough, Kevin J,Kim, Hye-Sook,Wataya, Yusuke
, p. 5979 - 5989 (2007/10/03)
Ozone-mediated cyclization of a series of unsaturated hydroperoxides 7, prepared from dienes 2, afforded the corresponding yingzhaosu A analogues 9 in moderate to high yield. X-Ray crystallographic analysis of two yingzhaosu A analogues, endo-9f and 13, showed that the 2,3-dioxabicyclo[3.3.1]nonane system adopts a chair-boat arrangement. Subsequent treatment of endoperoxides 9 with Ag2O/MeI afforded the expected methyldioxy-substituted cyclic peroxides 14, several of which showed notable anti-malarial activity against P. falciparum in vitro.
