Synthesis of vitisin A & D enabled by a persistent radical equilibrium
| Autor: | Ethan J Strobel, Markus Griesser, Mitchell H. Keylor, Kevin J Romero, Corey R. J. Stephenson, Derek A. Pratt, Xu Zhu |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Molecular Structure
Extramural Stereochemistry Dimer Radical Total synthesis General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Catalysis Article 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry chemistry Phenols Molecule Humans Isomerization Biogenesis Benzofurans |
| Zdroj: | J Am Chem Soc |
| Popis: | The first total synthesis of the resveratrol tetramers vitisin A and vitisin D is reported. Electrochemical generation and selective dimerization of persistent radicals is followed by thermal isomerization of the symmetric C8b–C8c dimer to the C3c–C8b isomer, providing rapid entry into the vitisin core. Computational results suggest that this synthetic approach mimics Nature’s strategy for constructing these complex molecules. Sequential acid-mediated rearrangements consistent with the proposed biogenesis of these compounds afford vitisin A and vitisin D. The rapid synthesis of these complex molecules will allow for further study of their pharmacological potential. |
| Databáze: | OpenAIRE |
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