TY - JOUR
T1 - Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals
AU - Nonami, Yuji
AU - Tokuyasu, Takahiro
AU - Masuyama, Araki
AU - Nojima, Masatomo
AU - McCullough, Kevin J.
AU - Kim, Hye Sook
AU - Wataya, Yusuke
N1 - Funding Information:
This work was supported in part by a Grant-in-Aid for Scientific Research on Priority Areas (10153238 and 10166211) from the Ministry of Education, Science, Culture and Sports of Japan.
PY - 2000/6/12
Y1 - 2000/6/12
N2 - Treatment of unsaturated hydroperoxy peracetals with bis(sym- collidine)iodine(I) hexafluorophosphate affords a series of iodine-containing spiro-1,2,4,5-tetraoxacycloalkane derivatives in high yield. In addition, ozonolysis of unsaturated hydroperoxy peracetals in AcOH-CH2Cl2 also results in the formation of spiro-1,2,4,5-tetraoxacycloalkanes. Two of the new compounds, 3-methyl-3,methyldioxy-1,2,6,7-tetraoxaspiro[7.11]nonadecane and dimethyl-4-iodo-1,2,6,7-tetraoxaspiro[7.11]nonadecane, exhibit significant in vitro antimalarial activity against P. falciparum with EC50 values of ca. 10-7 M. (C) 2000 Elsevier Science Ltd.
AB - Treatment of unsaturated hydroperoxy peracetals with bis(sym- collidine)iodine(I) hexafluorophosphate affords a series of iodine-containing spiro-1,2,4,5-tetraoxacycloalkane derivatives in high yield. In addition, ozonolysis of unsaturated hydroperoxy peracetals in AcOH-CH2Cl2 also results in the formation of spiro-1,2,4,5-tetraoxacycloalkanes. Two of the new compounds, 3-methyl-3,methyldioxy-1,2,6,7-tetraoxaspiro[7.11]nonadecane and dimethyl-4-iodo-1,2,6,7-tetraoxaspiro[7.11]nonadecane, exhibit significant in vitro antimalarial activity against P. falciparum with EC50 values of ca. 10-7 M. (C) 2000 Elsevier Science Ltd.
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U2 - 10.1016/S0040-4039(00)00688-2
DO - 10.1016/S0040-4039(00)00688-2
M3 - Article
AN - SCOPUS:0034640840
VL - 41
SP - 4681
EP - 4684
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 23
ER -