FIRST ASYMMETRIC TOTAL SYNTHESIS OF (-)-ISOSTEMONAMINE AND KINETIC ANALYSIS OF ITS ISOMERIZATIONS

The first asymmetric total synthesis of (-)-isostemonamine is reported herein. The key reactions include the regioselective oxidation of the diketone, which is reported to be an intermediate in our synthesis of (-)-stemonamine. The chiral high-performance liquid chromatography (HPLC) analysis of the racemization and epimerization of (-)-isostemonamine revealed that isostemonamine isomerizes significantly faster than stemonamine.