Publications

96. Asymmetric Total Synthesis of Propindilactone

   


Lin You, Xin-Ting Liang, Lingmin Xu, Yue-Fan Wang, Jia-Jun Zhang, Qi Su, Yuanhe Li, Bo Zhang, Shou-Liang Yang, Jia-Hua Chen*, and Zhen Yang*
J. Am. Chem. Soc., 2015, 137, 10120.

• Highlighted in Synfacts, 2015, 11, 1022.

A concise total synthesis of (+)-propindilactone G, a nortriterpenoid isolated from the stems of Schisandra propinqua var. propinqua, has been achieved for the first time. The key steps of the synthesis include an asymmetric Diels–Alder reaction, a Pauson–Khand reaction, a Pd-catalyzed reductive hydrogenolysis reaction, and an oxidative heterocoupling reaction. These reactions enabled the synthesis of (+)-propindilactone G in only 20 steps. As a consequence of our synthetic studies, the structure of (+)-propindilactone G has been revised.
Abstract