Ellagitannin Chemistry. the First Synthesis of Dehydrohexahydroxydiphenoate Esters from Oxidative Coupling of Unetherified Methyl Gallate

Stéphane Quideau, Ken S. Feldman

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Abstract

A simple o-chloranil-mediated oxidative dimerization of methyl gallate in anhydrous ether furnishes a dimethyl dehydrohexahydroxydiphenoate (DHHDP) product as a pale yellow precipitate in good yield. This methyl gallate dehydrodimer rapidly rearranges in acetone to give a mixture of two additional DHHDP regioisomers. One of these species corresponds to the isomer of the dehydro-hexahydroxydiphenoyl group commonly observed in dehydroellagitannin natural products. Sodium dithionite-mediated reduction of the initially formed dimethyl dehydrohexahydroxydiphenoate and/ or its derived regioisomers efficiently furnishes dimethyl hexahydroxydiphenoate (HHDP). Addition of N-(carbobenzyloxy)-L-cysteine benzyl ester to dimethyl dehydrohexahydroxydiphenoate(s) in THF solution produces two diastereomeric 3-S-cysteinyl derivatives of dimethyl hexahydroxydiphenoate.

Original languageEnglish (US)
Pages (from-to)8809-8813
Number of pages5
JournalJournal of Organic Chemistry
Volume62
Issue number25
DOIs
Publication statusPublished - Jan 1 1997

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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