3 years ago

Formal Total Synthesis of (±)-Lycojaponicumin C

Formal Total Synthesis of (±)-Lycojaponicumin C
Nan Zheng, Lijie Zhang, Jianxian Gong, Zhen Yang
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01154

DOI: 10.1021/acs.orglett.7b01154

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