Ellagitannin Chemistry. The First Total Chemical Synthesis of an O (2),O (3)-Galloyl-Coupled Ellagitannin, Sanguiin H-5

Ken S. Feldman; Aruna Sambandam

doi:10.1021/jo00130a016

Ellagitannin Chemistry. The First Total Chemical Synthesis of an O (2),O (3)-Galloyl-Coupled Ellagitannin, Sanguiin H-5

Ken S. Feldman, Aruna Sambandam

Chemistry

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52 Scopus citations

Abstract

The biomimetic synthesis of sanguiin H-5 (1) was accomplished through the diastereoselective formation of the crucial biphenyl carbon-carbon bond between galloyl moieties at the O (2) and O (3) positions of an appropriately protected glucose-derived precursor. Furthermore, the /3-anomeric galloyl linkage was established with complete stereochemical control.

Original language	English (US)
Pages (from-to)	8171-8178
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	60
Issue number	25
DOIs	https://doi.org/10.1021/jo00130a016
State	Published - Dec 1 1995

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00130a016

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abstract = "The biomimetic synthesis of sanguiin H-5 (1) was accomplished through the diastereoselective formation of the crucial biphenyl carbon-carbon bond between galloyl moieties at the O (2) and O (3) positions of an appropriately protected glucose-derived precursor. Furthermore, the /3-anomeric galloyl linkage was established with complete stereochemical control.",

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N2 - The biomimetic synthesis of sanguiin H-5 (1) was accomplished through the diastereoselective formation of the crucial biphenyl carbon-carbon bond between galloyl moieties at the O (2) and O (3) positions of an appropriately protected glucose-derived precursor. Furthermore, the /3-anomeric galloyl linkage was established with complete stereochemical control.

AB - The biomimetic synthesis of sanguiin H-5 (1) was accomplished through the diastereoselective formation of the crucial biphenyl carbon-carbon bond between galloyl moieties at the O (2) and O (3) positions of an appropriately protected glucose-derived precursor. Furthermore, the /3-anomeric galloyl linkage was established with complete stereochemical control.

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Ellagitannin Chemistry. The First Total Chemical Synthesis of an O (2),O (3)-Galloyl-Coupled Ellagitannin, Sanguiin H-5

Abstract

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