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 |
| DOIs | |
| Publication status | Published - Jun 12 2000 |
| Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Nonami, Y., Tokuyasu, T., Masuyama, A., Nojima, M., McCullough, K. J., Kim, H. S., & Wataya, Y. (2000). Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals. Tetrahedron Letters, 41(23), 4681-4684. https://doi.org/10.1016/S0040-4039(00)00688-2