Stereoselective synthesis of terpinen-4-ol-based aminoalcohols

Abstract

Terpinen-4-ol 1, a monoterpene, is found as the main component of essential oils isolated from cassumunar ginger and tea tree, exhibits different biological activities such as anticancer, anti-inflammatory, antibacterial and antiviral. In this paper chemical transformation of terpinen4-ol 1 is investigated with the aim to synthesize its new derivatives for the further application as potential candidates in drug discovery. Stereoselective synthesis of aminodiols 3-6 derived from terpinen-4-ol 1 was achieved with good yields. Two steps procedure of chemical transformation of terpinen-4-ol 1 to aminodiols 3-6 were performed by the stereoselective Payne epoxidation reaction of allyl alcohol 1 followed by the regioselective lithium perchlorate-catalyzed oxirane ring opening of epoxy alcohol 2 with benzyl amines. Obtained products were characterized by NMR analysis including two dimensional measurements.