Synthesis of novel polar derivatives of the antimalarial endoperoxides ascaridole and dihydroascaridole

Abstract

Novel polar derivatives of the antimalarial endoperoxide ascaridole were synthesized based on the zeolite NaY-promoted isomerization of perillyl and nopol derivatives to conjugated cyclohexadienes, followed by reaction with singlet oxygen. Several unsaturated endoperoxides were in situ reduced with diimide to form dihydroascaridole derivatives, as well.