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    Author(s): Seiji Ohara; Richard W. Hemingway
    Date: 1991
    Source: Journal of Wood Chemistry & Technology 11(2):195-208
    Publication Series: Miscellaneous Publication
    PDF: View PDF  (1.8 MB)

    Description

    Reaction of (+ )-catechin at pH 12 and 40 DC results in the stereoselective (if not stereospecific) formation of an enolic form of 1-[6-(3',4'-dihydroxyphenyl)-7-hydroxybicyclo[3.3.1]nonane-2,4,9-trione-3-yl]-1-(3,4-dihyroxyphenyl)-3-(2,-4,6-trihydroxyphenyl)-propan-2-ol. The n.m.r. chemical shift assignments determined by a variety of two-dimensional experiments permit a conclusion that the compound is one of four diastereoisomers possible from reaction of the two quinone methide intermediates. Stereoselectivity in the formation of this compound can be accounted for by preference for Re-face attack on both 2-C's of the quinone methides involved in the formation of the molecule.

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    Citation

    Ohara, Seiji; Hemingway, Richard W. 1991. Condensed tannins: The formation of a diarylpropanol-catechinic acid dimer from base-catalyzed reactions of (+)-catechin. Journal of Wood Chemistry & Technology 11(2):195-208

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