Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 4681-4684 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 41 |
| Issue number | 23 |
| Publication status | Published - Jun 12 2000 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals. / Nonami, Yuji; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; McCullough, Kevin J.; Kim, Hye-Sook; Wataya, Yusuke.
In: Tetrahedron Letters, Vol. 41, No. 23, 12.06.2000, p. 4681-4684.Research output: Contribution to journal › Article
}
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
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.
UR - http://www.scopus.com/inward/record.url?scp=0034640840&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0034640840&partnerID=8YFLogxK
M3 - Article
VL - 41
SP - 4681
EP - 4684
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 23
ER -