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

✍ Scribed by Yuji Nonami; Takahiro Tokuyasu; Araki Masuyama; Masatomo Nojima; Kevin J McCullough; Hye-Sook Kim; Yusuke Wataya

• Book ID: 104210412
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 165 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00688-2

✦ Synopsis

Treatment of unsaturated hydroperoxy peracetals with bis(sym-collidine)iodine(I) hexa¯uorophosphate aords a series of iodine-containing spiro-1,2,4,5-tetraoxacycloalkane derivatives in high yield. In addition, ozonolysis of unsaturated hydroperoxy peracetals in AcOH±CH 2 Cl 2 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 signi®cant in vitro antimalarial activity against P. falciparum with EC 50 values of ca. 10 ^7 M.