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

Ken S. Feldman; Susan M. Ensel

doi:10.1021/ja00087a022

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

Ken S. Feldman, Susan M. Ensel

Chemistry

Research output: Contribution to journal › Article › peer-review

75 Scopus citations

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 language	English (US)
Pages (from-to)	3357-3366
Number of pages	10
Journal	Journal of the American Chemical Society
Volume	116
Issue number	8
DOIs	https://doi.org/10.1021/ja00087a022
State	Published - Apr 1 1994

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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

Abstract

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