Ellagitannin chemistry. Syntheses of tellimagrandin II and a dehydrodigalloyl ether-containing dimeric gallotannin analogue of coriariin A

Ken S. Feldman, Kiran Sahasrabudhe

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

The first chemical synthesis of the naturally occurring ellagitannin tellimagrandin II is reported. Key steps of the synthesis include the atropselective oxidative coupling of suitably protected galloyl rings at the O(4) and O(6) positions of a glucopyranose core, and the stereoselective acylation of the derived anomeric alcohol with a galloyl chloride. In addition, the synthesis of a novel gallotannin-ellagitannin hybrid is described. This dimeric construct relied on a hetero-Diels-Alder cycloaddition/reductive rearrangement sequence to deliver the intact skeleton from a monomeric pentagalloylglucose-based orthoquinone.

Original languageEnglish (US)
Pages (from-to)209-216
Number of pages8
JournalJournal of Organic Chemistry
Volume64
Issue number1
DOIs
StatePublished - Jan 8 1999

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Hydrolyzable Tannins
Ether
Acylation
Cycloaddition
Chlorides
Alcohols
tellimagrandin II
ellagitannin

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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abstract = "The first chemical synthesis of the naturally occurring ellagitannin tellimagrandin II is reported. Key steps of the synthesis include the atropselective oxidative coupling of suitably protected galloyl rings at the O(4) and O(6) positions of a glucopyranose core, and the stereoselective acylation of the derived anomeric alcohol with a galloyl chloride. In addition, the synthesis of a novel gallotannin-ellagitannin hybrid is described. This dimeric construct relied on a hetero-Diels-Alder cycloaddition/reductive rearrangement sequence to deliver the intact skeleton from a monomeric pentagalloylglucose-based orthoquinone.",
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Ellagitannin chemistry. Syntheses of tellimagrandin II and a dehydrodigalloyl ether-containing dimeric gallotannin analogue of coriariin A. / Feldman, Ken S.; Sahasrabudhe, Kiran.

In: Journal of Organic Chemistry, Vol. 64, No. 1, 08.01.1999, p. 209-216.

Research output: Contribution to journalArticle

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