Stereocontrolled synthesis of fluorosqualenes and fluoroepoxy-squalenes as inhibitors of squalene epoxidase and 2,3-oxidosqualene cyclase

Abstract

Z-Fluorosqualene derivatives having one or more fluorine atoms at the terminal methyls of the squalene skeleton have been synthesized. A highly stereoselective synthesis, based on a Wittig reaction, was developed together with a new method for obtaining bifunctional derivatives of squalene. The compounds tested showed poor inhibitory activity on squalene epoxidase and 2,3-oxidosqualene cyclase from microsomes of Saccharomyces cerevisiae, Candida albicans and rat liver, and on S. cerevisiae and 3T3 fibroblast cell cultures.