Synthesis of 4-O-acetyl-L-rhodinopyranose via a tandem Sharpless asymmetric dihydroxylation/lipase-catalyzed transesterification

Article abstract of DOI:10.1016/0040-4039(95)00778-B

An enantioselective synthesis of the trideoxy sugar 4-O-acetyl-L-rhodinopyranose (7) is described. A key feature of the synthetic strategy is a Sharpless asymmetric dihydroxylation followed by a lipase-mediated mono-esterification of the resultant diol (3 → 4 → 6).