ja5b06480_si_003.pdf (6.1 MB)
Asymmetric Total Synthesis of Propindilactone G
journal contribution
posted on 2015-08-19, 00:00 authored by Lin You, Xin-Ting Liang, Ling-Min Xu, Yue-Fan Wang, Jia-Jun Zhang, Qi Su, Yuan-He Li, Bo Zhang, Shou-Liang Yang, Jia-Hua Chen, Zhen YangA 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.