Abstract
Several optically active 3,4-dihydroxy-2-hydroxymethyl pyrrolidines are potent α-glycosidase inhibitors; for example, 1,4-dideoxy-1,4-imino-D-lyxitol (1) is a powerful inhibitor of α-galactosidase.1 Furthermore, pyrrolidine 1 can be easily converted into the indolizidine alkaloid swainsonine to which it is structurally related.2 (-) Swainsonine exhibits α-D-mannosidase inhibitory activity and immunoregulatory activity. Certain swainsonine stereoisomers have glycosidase inhibitory activity as well, and therefore have attracted considerable interest.3 1,4-Dideoxy-1,4-imino-L-lyxitol (2) (enantiomer of 1) could be of biological interest. This communication describes the first synthesis of 2, starting from D-ribonolactone.
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