TY - JOUR
T1 - Synthetic methods for unsymmetrically-substituted 1,2,4,5-tetroxanes and of 1,2,4,5,7-pentoxocanes
AU - Kim, Hye Sook
AU - Tsuchiya, Kaoru
AU - Shibata, Yasuharu
AU - Wataya, Yusuke
AU - Ushigoe, Yoshihiro
AU - Masuyama, Araki
AU - Nojima, Màsatomo
AU - McCullough, Kevin J.
PY - 1999
Y1 - 1999
N2 - Ozonolysis of vinyl ethers la-c in the presence of hydrogen peroxide in diethyl ether gave the corresponding 1,1-bis(hydroperoxide)s 2a-c. Subsequent trimethylsilylation, followed by the TMSOTf-catalyzed cyclocondensation with carbonyl compounds gave the unsymmetrically-substituted 1,2,4,5-tetroxanes 5-14. Similarly, the 1,2,4,5,7-pentoxocanes 18,19 were prepared by the reaction of an a,a'-bis(trimethylsilylperoxy) ether 17 and carbonyl compounds. The tetroxane 14 showed notable antimalarial activity in vitro and HI vivo.
AB - Ozonolysis of vinyl ethers la-c in the presence of hydrogen peroxide in diethyl ether gave the corresponding 1,1-bis(hydroperoxide)s 2a-c. Subsequent trimethylsilylation, followed by the TMSOTf-catalyzed cyclocondensation with carbonyl compounds gave the unsymmetrically-substituted 1,2,4,5-tetroxanes 5-14. Similarly, the 1,2,4,5,7-pentoxocanes 18,19 were prepared by the reaction of an a,a'-bis(trimethylsilylperoxy) ether 17 and carbonyl compounds. The tetroxane 14 showed notable antimalarial activity in vitro and HI vivo.
UR - http://www.scopus.com/inward/record.url?scp=0000349616&partnerID=8YFLogxK
M3 - Article
SN - 0300-922X
SP - 1867
EP - 1870
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 13
ER -