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
