Biosynthetically, resveratrol oligomerization is believed to proceed via controlled single electron oxidation processes, resulting in the union of radical intermediates in a regio- and stereoselective manner. Despite the number of resonance hybrids available to the resveratrol phenoxy radical, they primarily dimerize in a chemo- and regioselective manner, yielding isomeric quinone methide intermediates. Although there are hundreds of resveratrol oligomers known, these natural products are characterized by highly conserved carbogenic cores, which are conceivably generated through cyclization, isomerization, and oligomerization reactions of these important quinone methide intermediates. We envisioned that access to the inherent reactivity of these intermediates would enable the modular and divergent syntheses of a large number of molecules within this class. Acting on this hypothesis, we have developed a robust biomimetic synthetic route to the natural products quadrangularin A and pallidol and are pursuing higher order oligomers utilizing our strategy.Importantly, this synthetic route enables controlled access to a range of polyphenolic architectures and natural product analogs. We have established a collaboration with Prof. Derek Pratt of the University of Ottawa, an expert in free radical oxidation chemistry who will rigorously evaluate all of the compounds we prepare in this project for their antioxidant properties.

Concise biomimetic synthesis of resveratrol oligomers utilizing versatile <i>?p</i>?-quinone methide intermediates

248th National Meeting (2014)

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Concise biomimetic synthesis of resveratrol oligomers utilizing versatile ?p?-quinone methide intermediates