Skip to Main Content
Due to a lapse in federal funding, this USDA website will not be actively updated. Once funding has been reestablished, online operations will continue.
Condensed tannins: A novel rearrangement of procyanidins and prodelphinidins in thiolytic cleavageAuthor(s): G. Wayne McGraw; Jan P. Steynberg; Richard W. Hemingway
Source: Tetrahedron Letters 34(6):987-990
Publication Series: Miscellaneous Publication
PDF: View PDF (1.2 MB)
DescriptionConditions 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.
- You may send email to firstname.lastname@example.org to request a hard copy of this publication.
- (Please specify exactly which publication you are requesting and your mailing address.)
- We recommend that you also print this page and attach it to the printout of the article, to retain the full citation information.
- This article was written and prepared by U.S. Government employees on official time, and is therefore in the public domain.
CitationMcGraw, 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
- Acid-catalyzed rearrangements of flavan-4-phloroglucinol derivatives to novel 6-hydroxyphenyl-6a,llb-dihydro-6H-benzofuro[2,3-c]-chromenes and hydroxyphenyl-3,2'-spirobi[dihydro[l]benzofurans]
- Density functional theory study of spirodienone stereoisomers in lignin
- Kinetics of acid-catalyzed cleavage of procyanindins
XML: View XML