Potent glycosidase inhibitors via hetero Diels-Alder reactions: Asymmetric synthesis of 5-methyl-trihydroxypyrrolidines

Article abstract of DOI:10.1016/S0957-4166(97)00008-6

Some straightforward chemical transformations of oxazine diol 4, which was obtained from sorbaldehyde 2 by an asymmetric hetero Diels-Alder reaction followed by osmylation, led to the protected dihydroxypyrrolidine-aldehyde 8a and, after basic epimerisation, to 8b. Reduction of the aldehyde moiety and deprotection gave the potent glycosidase inhibitors 2,5,6-trideoxy-2,5-imino-D-altritol and D-allitol 9a and 9b.