Galloyl-derived orthoquinones as reactive partners in nucleophilic additions and Diels-Alder dimerizations: A novel route to the dehydrodigalloyl linker unit of agrimoniin-type ellagitannins

Ken S. Feldman, Stéphane Quideau, Heidi M. Appel

Research output: Contribution to journalArticle

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Abstract

Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.

Original languageEnglish (US)
Pages (from-to)6656-6665
Number of pages10
JournalJournal of Organic Chemistry
Volume61
Issue number19
DOIs
Publication statusPublished - Sep 20 1996

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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