Ellagitannin Chemistry. The First Total Chemical Synthesis of an Ellagitannin Natural Product, Tellimagrandin I

Ken S. Feldman, Susan M. Ensel, Robert D. Minard

Research output: Contribution to journalArticlepeer-review

64 Scopus citations

Abstract

Tellimagrandin I was synthesized by two different biogenetically patterned routes. One route featured diastereoselective galloyl ester coupling between the O(4) and O(6) galloyl moieties in a glucose-derived substrate bearing additional protected galloyl groups on O(2) and O(3). The second route relied on a completely diastereoselective and regioselective Pb(OAc)4-based oxidative coupling exclusively between the O(4) and O(6) galloyl esters in a glucose-derived substrate featuring oxidation sensitive galloyl groups on O(2)-O(6). Molecular mechanics-based conformational analysis provides a rationale for the observed selectivity.

Original languageEnglish (US)
Pages (from-to)1742-1745
Number of pages4
JournalJournal of the American Chemical Society
Volume116
Issue number5
DOIs
StatePublished - Mar 1 1994

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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