Chemoenzymatic total synthesis of potent HIV RNase H inhibitor (−)-1,3,4,5-tetragalloylapiitol

Starting from racemic dimethyl 2-acetoxy-3-methylenesuccinate, the chemoenzymatic facile total synthesis of (−)-1,3,4,5-tetragalloylapiitol has been demonstrated via an efficient lipase catalyzed resolution followed by a DIBAL reduction-double gallyolation, osmium tetroxide dihydroxylation-double gallyolation, and reductive global O-benzyl deprotection pathway.