Ellagitannin chemistry. First total synthesis of the 2,3- and 4,6-coupled ellagitannin pedunculagin

Ken S. Feldman, Randall S. Smith

Research output: Contribution to journalArticle

68 Scopus citations

Abstract

The biomimetic synthesis of pedunculagin (1) was accomplished through the sequential diastereoselective formation of two biphenyl C-C bonds. The synthesis strategy employed is predicated on extensive conformational modeling and involves initial oxidative coupling of the galloyl moieties at the O(2) and O(3) positions of an appropriately protected glucose-derived core, followed by installation and oxidative coupling of galloyl esters at the O(4) and O(6) positions.

Original languageEnglish (US)
Pages (from-to)2606-2612
Number of pages7
JournalJournal of Organic Chemistry
Volume61
Issue number8
DOIs
StatePublished - Apr 19 1996

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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