One of the research topics of Sarlah’s group at Rice University is visible light-mediated dearomatization of aromatic rings that swiftly converts a planar ring into a partially unsaturated, and functionalized intermediate. In their synthesis of Pancratistatins published in 2017, they show the synthetic capabilities of such a reaction by enantioselectively functionalizing a benzene ring into a disubstituted cyclohexadiene moiety.
Journal of the American Chemical Society, 139(44), 15656–15659.
A following two-step oxidation sequence sets the correct stereochemistry of the four newly introduced hydroxyl groups:
Comment on the regioselectivity, and absolute/relative stereochemistry of the two oxidation steps.
For reference:
Hernandez, L. W., Pospech, J., Klöckner, U., Bingham, T. W., & Sarlah, D. (2017).
Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene.
Journal of the American Chemical Society, 139(44), 15656–15659.
doi:10.1021/jacs.7b10351