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    Author(s): G. Wayne McGraw; Jan P. Steynberg; Richard W. Hemingway
    Date: 1993
    Source: Tetrahedron Letters 34(6):987-990
    Publication Series: Miscellaneous Publication
    PDF: View PDF  (1.2 MB)


    Conditions commonly used for the thiolytic cleavage of interflavanoid bonds of condensed tannins also result in cleavage of the C4 to C10 bond of flavan units. Subsequenet lectrophilic attack of the C4 carbocation on the C2' or C6' of the B-ring, and loss of phloroglucinol (the A-ring), result in the formation of a mixture of 1,3-dithiobenzyl-2,4,s,6-tetrahydroxy indane diastereomers.

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    McGraw, G. Wayne; Steynberg, Jan P.; Hemingway, Richard W. 1993. Condensed tannins: A novel rearrangement of procyanidins and prodelphinidins in thiolytic cleavage. Tetrahedron Letters 34(6):987-990

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