New trifluoromethylated sesquiterpenoids: synthesis, rearrangement, and biological activity

Abstract

Trifluoromethylated compounds are important pharmaceutical substances. However, the synthesis of fluorine-containing compounds having a complicated structure using classical synthetic methods is often problematic. In this work, we demonstrated the capacity of the isomerization reaction as an efficient and atom-economical tool for the synthesis of complex compounds using the natural sesquiterpenoid caryophyllene oxide as an example. The rearrangement pathways of 8-trifluoromethyl-4,5-epoxycaryophyllanyl-8-ol have been proposed. The synthesized sesquiterpenoids were demonstrated to have a great deal of potential as biologically active compounds possessing antiviral and antimicrobial properties.