364593-90-8Relevant academic research and scientific papers
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.
Synthesis and anti-malarial activity of yingzhaosu A analogues from unsaturated hydroperoxy acetals
Tokuyasu, Takahiro,Masuyama, Araki,Nojima, Masatomo,Kim, Hye-Sook,Wataya, Yusuke
, p. 3145 - 3148 (2007/10/03)
Ozonolysis of a vinyl ether 2, prepared from dihydrocarvone 1 (a 1:4 mixture of cis- and trans-isomer), in methanol gave two isomeric unsaturated hydroperoxy acetals cis- and trans-3. Iodonium ion- or ozone-mediated cyclizations of the hydroperoxide cis-3 gave the corresponding yingzhaosu A analogues 4 and 6 in moderate yields. The peroxide 8, obtained by the Ag2O- mediated methylation of 6, showed notable anti-malarial activity in vitro (IC50=1.0 x 10-7 M). (C) 2000 Elsevier Science Ltd.
