Abstract
Profisetinidins with 2,3-trans-3,4-trans-(-)-fisetinidol units are subject to stereospecific C-ring isomerization under mild basic conditions; whereas, those with 2,3-trans-3,4-cis “upper” units are susceptible to stereoselective pyran rearrangements. In the latter situation, the functionalized tetrahydropyranochromenes are accompanied by analogs in which the resorcinol A- and pyrocatechol B-ring have been interchanged. The formation of these ring interchanged compounds are explicable in terms of a unique 1,3-aryl migration in a quinone-methide intermediate, such a mechanism, however, requiring the inversion of the absolute configuration at the equivalent of 3-C(C) in the biflavanoid precursor. These base-catalyzed pyran rearrangements may have an important bearing on the industrial applications of condensed tannins.
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Ferreira, D., Steynberg, J.P., Burger, J.F.W., Young, D.A. (1989). Base-Catalyzed Pyran Rearrangements of Profisetinidins. In: Hemingway, R.W., Karchesy, J.J., Branham, S.J. (eds) Chemistry and Significance of Condensed Tannins. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-7511-1_17
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DOI: https://doi.org/10.1007/978-1-4684-7511-1_17
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