Synthesis of resveratrol tetramers via a stereoconvergent radical equilibrium
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...
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| Veröffentlicht in: | Science (American Association for the Advancement of Science) 2016-12, Vol.354 (6317), p.1260-1265 |
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| creator | Keylor, Mitchell H. Matsuura, Bryan S. Griesser, Markus Chauvin, Jean-Philippe R. Harding, Ryan A. Kirillova, Mariia S. Zhu, Xu Fischer, Oliver J. Pratt, Derek A. Stephenson, Corey R. J. |
| description | 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. |
| doi_str_mv | 10.1126/science.aaj1597 |
| format | Article |
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J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of resveratrol tetramers via a stereoconvergent radical equilibrium</atitle><jtitle>Science (American Association for the Advancement of Science)</jtitle><addtitle>Science</addtitle><date>2016-12-09</date><risdate>2016</risdate><volume>354</volume><issue>6317</issue><spage>1260</spage><epage>1265</epage><pages>1260-1265</pages><issn>0036-8075</issn><eissn>1095-9203</eissn><coden>SCIEAS</coden><abstract>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. 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| subjects | Benzofurans - chemical synthesis Biological Products - chemical synthesis Bonding strength Carbon Carbon - chemistry Carbon-carbon composites Chemistry Dimerization Fragments Free radicals Indolequinones - chemistry Organic chemicals Oxidation-Reduction Polymerization Polyphenols Radicals Resorcinols - chemical synthesis Stilbenes - chemical synthesis Synthesis Synthesis (chemistry) |
| title | Synthesis of resveratrol tetramers via a stereoconvergent radical equilibrium |
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