Abstract
Base-catalysed rearrangement of the oxazine-carboxylate 8, obtained from pentadienoic acid 4 by asymmetric hetero-Diels-Alder reaction followed by simple chemical transformations, led to the protected trihydroxy-proline 9. Using various reduction conditions, the potent glycosidase inhibitors 1,4-dideoxy-1,4-imino-D-lyxitol D-1 and 1,4-dideoxy-1,4-imino-L-ribitol L-2 were obtained.
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