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

Article abstract of DOI:10.1021/jo00130a016

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 β-anomeric galloyl linkage was established with complete stereochemical control.