Due to their interesting biological activity and fascinating structures, the resveratrol oligomer class of natural products remains a challenging and important area of research for synthetic chemists. It was discovered after some optimization, that the deprotonation of resveratrol analogue 1  , sufficiently decreased the redox potential of 1  to allow for an ambient temperature aerobic oxidation of 1  to the linear dimer 2  in 50-55% yield. This dimer can be cyclized using BF3OEt2 to form the carbon skeleton of quadrangularin A (3  ).

Biomimetic synthesis of resveratrol dimers

244th National Meeting (2012)

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