Synthesis of Resveratrol Tetramers via a Stereoconvergent Radical Equilibrium
| Autor: | Ryan A. Harding, Mariia S. Kirillova, Jean-Philippe R. Chauvin, Derek A. Pratt, Bryan S. Matsuura, Mitchell H. Keylor, Oliver J. Fischer, Corey R. J. Stephenson, Xu Zhu, Markus Griesser |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
Stereochemistry
Radical Radical polymerization Oxidative phosphorylation Resveratrol 010402 general chemistry Cleavage (embryo) 01 natural sciences Article chemistry.chemical_compound Stilbenes Indolequinones Benzofurans Biological Products Multidisciplinary 010405 organic chemistry Resorcinols Small molecule Quinone methide Carbon 0104 chemical sciences chemistry Dimerization Oxidation-Reduction Biogenesis |
| Popis: | Catching a break in polyphenol synthesis Chemical synthesis is usually rather different from playing with a modeling kit. If two large fragments of a molecule are not properly oriented, it is not typically possible to break them apart, rotate one, and then paste them back together. Yet that is precisely the trick that Keylor et al. used to synthesize two plant-derived polyphenols. Resveratrol forms a variety of dimers, trimers, and tetramers. When one central carbon-carbon bond links the fragments, it is weak enough to break spontaneously and reversibly at room temperature. The authors leveraged this equilibrium to generate an efficient route to two of the tetramers, nepalensinol B and vateriaphenol C. Science , this issue p. 1260 |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|