Ellagitannin Chemistry. Preparative and Mechanistic Studies of the Biomimetic Oxidative Coupling of Galloyl Esters

Ken S. Feldman, Susan M. Ensel

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

The construction of strictly the (S)-hexahydroxydiphenyl (HHDP) unit via biomimetic cyclization of suitably protected glucose-derived digalloyl esters has been achieved in good yield. Studies on substrates of increasing complexity utilizing a range of oxidants (Pb(OAc)4, VOF3, Tl2O3) have helped define the scope and limitations of this approach to ellagitannin synthesis. Computer modeling of key cyclization precursors helped elucidate the molecular-level structural details which undergird the Haslam/Schmidt biosynthesis model for this class of naturally occurring secondary plant metabolites.

Original languageEnglish (US)
Pages (from-to)3357-3366
Number of pages10
JournalJournal of the American Chemical Society
Volume116
Issue number8
DOIs
StatePublished - Apr 1 1994

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Oxidative Coupling
Biomimetics
Cyclization
Esters
Biosynthesis
Metabolites
Oxidants
Glucose
Substrates
ellagitannin

All Science Journal Classification (ASJC) codes

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

Cite this

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Ellagitannin Chemistry. Preparative and Mechanistic Studies of the Biomimetic Oxidative Coupling of Galloyl Esters. / Feldman, Ken S.; Ensel, Susan M.

In: Journal of the American Chemical Society, Vol. 116, No. 8, 01.04.1994, p. 3357-3366.

Research output: Contribution to journalArticle

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