Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals

Yuji Nonami; Takahiro Tokuyasu; Araki Masuyama; Masatomo Nojima; Kevin J. McCullough; Hye Sook Kim; Yusuke Wataya

doi:10.1016/S0040-4039(00)00688-2

Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals

Yuji Nonami, Takahiro Tokuyasu, Araki Masuyama, Masatomo Nojima, Kevin J. McCullough, Hye Sook Kim, Yusuke Wataya

Research output: Contribution to journal › Article

26 Citations (Scopus)

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	https://doi.org/10.1016/S0040-4039(00)00688-2
Publication status	Published - Jun 12 2000
Externally published	Yes

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ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

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

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

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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.",

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AU - McCullough, Kevin J.

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Access to Document

10.1016/S0040-4039(00)00688-2