Ellagitannin chemistry. The first total chemical synthesis of an O(2),O(3)-galloyl-coupled ellagitannin, sanguiin H-5

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