Enantiospecific Syntheses of 2,5-Dideoxy-2,5-imino-D-mannitol and -L-iditol from D-Mannitol

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Abstract
DMDP (2,5-dideoxy-2,5-imino-D-mannitol; 1) and 2,5-dideoxy-2,5-imino-L-iditol (2) have been synthesized in an enantiospecific way, starting from D-mannitol. Key transformations included the C-2 and C-5 configuration inversion of D-mannitol and the stereocontrolled cyclization of C 2 symmetrical 2,5-bis(hydroxymethyl)-3,4-dihydroxypyrrolidines 1 and 2.