Condensed tannins: A novel rearrangement of procyanidins and prodelphinidins in thiolytic cleavage

G. Wayne McGraw; Jan P. Steynberg; Richard W. Hemingway

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Condensed tannins: A novel rearrangement of procyanidins and prodelphinidins in thiolytic cleavage

Informally Refereed

Authors:

G. Wayne McGraw, Jan P. Steynberg, Richard W. Hemingway

Year:

1993

Type:

Scientific Journal

Station:

Southern Research Station

Source:

Tetrahedron Letters 34(6):987-990

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Abstract

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.

Citation

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