A rapid total synthesis of an ellagitannin

Article abstract of DOI:10.1021/jo00088a046

The ellagitannins are galloyl esters of glucose that contain at least one chiral biaryl (digalloyl) subunit. Included in this family are the tellimagrandins (1-3). The first asymmetric synthesis of (S)-4,4',5,5',6,6'-hexamethoxy-2,2'-diphenic acid, a ubiquitous subunit in ellagitannins, is reported by utilization of an intermolecular oxazoline-mediated asymmetric Ullmann coupling. Attachment of this acid to an appropriate glucose core resulted in the synthesis of an ellagitannin.