Abstract
The phenolic methyl ethers of flavan-3-ols, 4-arylflavan-3-ols, and (-)-fisetinidol-(4,8)-(+)-catechin biflavanoids are susceptible to regio- and stereoselective oxygenation at C-4 in satisfactory yields with DDQ in CHCl3-MeOH solution and with K2S2O8 in aq. CH3CN solution. A mechanistic rationale is proposed to account for the observed stereos-electivity evident in the product distribution for both oxidants. The 4-functionalized analogues are of both synthetic and degradative significance in condensed tannin chemistry.
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Mouton, C.H.L., Ferreira, D., Steenkamp, J.A. (1992). Stereoselective Oxygenation of Flavan-3-Ols, 4-Arylflavan-3-Ols, and Profisetinidin Biflavanoids at C-4. In: Hemingway, R.W., Laks, P.E. (eds) Plant Polyphenols. Basic Life Sciences, vol 59. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3476-1_8
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DOI: https://doi.org/10.1007/978-1-4615-3476-1_8
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