First Total Synthesis of Highly Anti-Inflammatory Active Licochalcone D Through Water-Accelerated [3,3]-Sigmatropic Rearrangement

E-mail: jgjun@hallym.ac.krReceived September 14, 2012, Accepted October 4, 2012Licochalcones, derived from the dried roots of Glycyrrhiza inflata, have been reported to show variousbiological activities including antitumor, antiparasitic, antileishmanial, antioxidative, superoxide scavenging,antibacterial, and PTP1B activity. Licochalcone D has an allyl group on ring A instead of ring B, however, mostother natural licochalcones possess the group on ring B. Total synthesis of licochalcone D has not been reportedeven possessing the strongest anti-inflammatory activity. Therefore, the first total synthesis of licochalcone Dhas been developed by using water-accelerated [3,3]-sigmatropic rearrangement method.Key Words : Licochalcone D, Anti-inflammatory activity, Glycyrrhiza inflata, Water-accelerated [3,3]-sigma-tropic rearrangement, Licorice IntroductionLicorice, an herbal medicine prepared from the root ofsome Glycyrrhiza species containing various licochalcones,is one of the most popular folk medicine in the world.