Deguelin, as a rotenoid, has emerged as an attractive pharmacophore for chemprevention due to its effectiveness for both in vitro and in vivo... Show moreDeguelin, as a rotenoid, has emerged as an attractive pharmacophore for chemprevention due to its effectiveness for both in vitro and in vivo models. The biological activity and its structural complexity instigated the development of new synthetic technologies which could satisfy the increasing demand of deguelin, as well as broaden the diversity of the rotenoids. Here, a strategy of asymmetric acid-catalyzed annulations toward the enantioselective total synthesis of (-)-deguelin will be discussed. Several approaches were investigated to connect the chromene and phenolic moieties to create the pentacyclic rotenoid skeleton. Meanwhile, by collaborating with Professor Rajendra Mehta, several derivatives of deguelin were also made to study its bioactivity and interaction modes with specific proteins. M.S. in Chemistry, May 2013 Show less
