An ellagitannin, cercidinin A, was synthesized through both intramolecular coupling of gallates on a glucose moiety and double esterification of protected hexahydroxydiphenic acid to a diol. The total synthesis confirmed the revised structure of cercidinin A as 1,2,6-tri-O-galloyl-3,4-(R)-hexahydroxydiphenoyl (HHDP) β-D-glucose. This is the first synthesis of 3,4-HHDP-bridged ellagitannins and was achieved after overcoming two challenges: (1) full galloylation of β-glucose hindered the formation of the 3,4-HHDP group, and (2) the fully benzylated galloyl group, which is a routine component in ellagitannin synthesis, was not always appropriate. The solutions to these problems can be used to form a strategy for the synthesis of complex ellagitannins.