Tannins and Related Compounds. C. : Reaction of Dehydrohexahydroxydiphenic Acid Esters with Bases, and Its Application to the Structure Determination of Pomegranate Tannins, Granatins A and B

概要

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Some novel reactions of dehydrohexahydroxydiphenic acid esters [e.g., geraniin (1)] with bases are presented. Namely, treatment of 1 with triethylamine or sodium benzenesulfinate in acetonitrile caused a benzylic acid-type rearrangement to yield a brevifolin carboxylic acid derivative (3). On the other hand, treatment of 1 with pyridine gave a tetrahydroxydibenzofuran derivative (8), whereas reaction with aqueous sodium hydroxide cleaved the carbon-carbon linkage to yield a dehydrochebulic acid ester (10).The application of these reactions to granatins A and B, the major tannins in pomegranate, unequivocally established their structures (13 and 11,respectively).
社団法人日本薬学会の論文
1990-09-25