ortho-Quinone Methide Cyclizations Inspired by the Busseihydroquinone Family of Natural Products
2019
Burchill, Laura | Pepper, Henry P. | Sumby, Christopher J. | George, Jonathan H.
A series of cascade reactions of o-quinone methides have been developed based on the proposed biosynthesis of busseihydroquinone and parvinaphthol meroterpenoid natural products. The polycyclic framework of the most complex family members, busseihydroquinone E and parvinaphthol C, was assembled by an intramolecular [4 + 2] cycloaddition of an electron-rich chromene substrate. The resultant cyclic enol ether underwent rearrangements under acidic or oxidative conditions, which led to a new total synthesis of rhodonoid D.
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