Journal
SCIENCE
Volume 354, Issue 6317, Pages 1260-1265Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aaj1597
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Funding
- NIH-National Institute of General Medical Sciences [R01-GM096129]
- Camille Dreyfus Teacher Scholar Award Program
- University of Michigan
- National Sciences and Research Council of Canada
- Canara Research Chairs program
- University of Ottawa
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Persistent free radicals have become indispensable in the synthesis of organic materials through living radical polymerization. However, examples of their use in the synthesis of small molecules are rare. Here, we report the application of persistent radical and quinone methide intermediates to the synthesis of the resveratrol tetramers nepalensinol B and vateriaphenol C. The spontaneous cleavage and reconstitution of exceptionally weak carbon-carbon bonds has enabled a stereoconvergent oxidative dimerization of racemic materials in a transformation that likely coincides with the biogenesis of these natural products. The efficient synthesis of higher-order oligomers of resveratrol will facilitate the biological studies necessary to elucidate their mechanism(s) of action.
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