129.Formal Total Synthesis of Hybocarpone Enabled by Visible-Light-Promoted Benzannulation

Wei Chen, Renyu Guo, Zhen Yang*, and Jianxian Gong*

J. Org. Chem., 2018, 83 (24), pp 15524–15532

The formal total synthesis of hybocarpone was achieved in eight steps from commercially available 1,2,4-trimethoxybenzene. Key transformations include a visible-light-promoted benzannulation to construct the key α-naphthol intermediate and a modified CAN-mediated dimerization/hydration cascade sequence to generate the vicinal all-carbon quaternary centers in a stereocontrolled manner. The total synthesis of boryquinone was also achieved in seven steps.