TY - JOUR
T1 - Yingzhaosu A analogues
T2 - Synthesis by the ozonolysis of unsaturated hydroperoxides, structural analysis and determination of anti-malarial activity
AU - Tokuyasu, Takahiro
AU - Masuyama, Araki
AU - Nojima, Masatomo
AU - McCullough, Kevin J.
AU - Kim, Hye Sook
AU - Wataya, Yusuke
PY - 2001/7/9
Y1 - 2001/7/9
N2 - 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. © 2001 Elsevier Science Ltd.
AB - 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. © 2001 Elsevier Science Ltd.
KW - Anti-malarial activity
KW - Ozone-mediated cyclization
KW - Unsaturated hydroperoxides
KW - Yingzhaosu A analogues
UR - http://www.scopus.com/inward/record.url?scp=0035833052&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)00557-9
DO - 10.1016/S0040-4020(01)00557-9
M3 - Article
SN - 0040-4020
VL - 57
SP - 5979
EP - 5989
JO - Tetrahedron
JF - Tetrahedron
IS - 28
ER -