Abstract: The [3+4] cycloaddition reaction between different dienes (cyclopentadiene, 2-methylfurane and furane) and haloketones formed their corresponding cycloadducts. Ozonolysis of the cycloadducts yielded the ozonides 3alpha ,5alpha -dimethyl-8,9,10-trioxatricyclo[5.2.1.1(2,6)]undecan-4-one (6), 2,3alpha ,5alpha -trimethyl-8,9,10,11-tetraoxatricyclo[5.2.1.1(2,6)]undecan-4-one (9), 2,3beta ,5beta -trimethyl-8,9,10,11-tetraoxatricyclo[5.2.1.1(2,6)]undecan-4-one (10, exo isomer), 2,3beta ,5beta -trimethyl-8,9,10,11-tetraoxatricyclo[5.2.1.1(2,6)]undecan-4-one (11, endo isomer), 3alpha -isopropyl-8,9,10,11-tetraoxatricyclo[5.2.1.1(2,6)]undecan-4-one (14). The antimalaria activity of the ozonides was evaluated "in vitro" against strain of Plasmodium falciparum, from Thailand.
Ozonides; [3+4] cycloaddition; oxyallyl cation; malaria
