Synthesis of resveratrol tetramers via a stereoconvergent radical equilibrium.
| Autor: | Keylor MH; Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109, USA., Matsuura BS; Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109, USA., Griesser M; Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie Private,Ottawa, Ontario K1N 6N5, Canada., Chauvin JR; Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie Private,Ottawa, Ontario K1N 6N5, Canada., Harding RA; Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109, USA., Kirillova MS; Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109, USA., Zhu X; Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109, USA., Fischer OJ; Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109, USA., Pratt DA; Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie Private,Ottawa, Ontario K1N 6N5, Canada. crjsteph@umich.edu dpratt@uottawa.ca., Stephenson CR; Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109, USA. crjsteph@umich.edu dpratt@uottawa.ca. |
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| Jazyk: | angličtina |
| Zdroj: | Science (New York, N.Y.) [Science] 2016 Dec 09; Vol. 354 (6317), pp. 1260-1265. |
| DOI: | 10.1126/science.aaj1597 |
| Abstrakt: | 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. (Copyright © 2016, American Association for the Advancement of Science.) |
| Databáze: | MEDLINE |
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