113.Formal Total Synthesis of (±)-Lycojaponicumin C

Nan Zheng, Lijie Zhang, Jianxian Gong*, and Zhen Yang*

Org. Lett., 2017, 19, 2921–2924

The formal total synthesis of (±)-lycojaponicumin C has been accomplished. Key transformations include a Rh-catalyzed formal [3 + 2] cycloaddition reaction to construct the bicyclic [3.3.0] scaffold bearing two vicinal quaternary carbon centers, a stereoselective γ-hydroxyl directed Michael addition to introduce the vinyl group at a bulky position, and a late-stage ring-closing metathesis reaction to form the cyclohexanone ring.