Abstract
A tactical combination of either ( S)- or ( R)-proline catalyzed aldol reaction followed by intramolecular reductive amination enabled the synthesis of a chiral pyrrolidine derivative with 3 contiguous stereocenters in only 2 synthetic steps, starting from achiral precursors. This product, obtainable in both enantiomeric forms, was further exploited as a common intermediate in total syntheses of the biologically active iminosugars: ( + )-swainsonine, (–)-swainsonine, ( + )-8- epi-swainsonine, and ( + )-dideoxy-imino-lyxitol.
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