Synthesis of Vitisins A and D Enabled by a Persistent Radical Equilibrium
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 c...
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| Veröffentlicht in: | Journal of the American Chemical Society 2020-04, Vol.142 (14), p.6499-6504 |
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| container_issue | 14 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 142 |
| creator | Romero, Kevin J Keylor, Mitchell H Griesser, Markus Zhu, Xu Strobel, Ethan J Pratt, Derek A Stephenson, Corey R. J |
| description | 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 enable further study of their pharmacological potential. |
| doi_str_mv | 10.1021/jacs.0c01714 |
| format | Article |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Benzofurans - chemical synthesis Humans Molecular Structure Phenols - chemical synthesis |
| title | Synthesis of Vitisins A and D Enabled by a Persistent Radical Equilibrium |
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