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Reductive elimination of alkoxy group in anthraquinone derivativesстатья
- Авторы: Tikhomirov A.S., Andreeva D.V., Shchekotikhin A.E.
- Журнал: Tetrahedron
- Том: 122
- Год издания: 2022
- Издательство: Pergamon Press Ltd.
- Местоположение издательства: United Kingdom
- DOI: 10.1016/j.tet.2022.132957
- Аннотация: Anthraquinone derivatives are constantly in a focus of synthetic chemists due to a diversity of valuable biological, photochemical and redox properties. However, quinone core limits applicability of chemical transformations making a search for new methods of modification of anthraquinones highly demanded. A convenient approach of regioselective reductive α-alkoxy group cleavage of anthraquinone derivatives was developed and evaluated. Most effectively transformation goes via a zinc reduction of quinone moiety and prototropic rearrangement in acidic media followed by the alkoxy group elimination. Strong donors in β-position of anthraquinone core are crucial for transformation and provide the elimination exclusively from α-position. The method simplifies an access to some bioactive 1,3-substituted anthraquinones and was applied for synthesis of natural products, e.g., rubiadin 1-methyl ether, anthragallol 1,2-dimethyl ether, and damnacanthol. © 2022 Elsevier Ltd
- Добавил в систему: Малошицкая Ольга Александровна