Synthesis of N‐Substituted (3S,4S)‐ and (3R,4R)‐Pyrrolidine‐3,4‐diols: Search for New Glycosidase Inhibitors

Abstract

AbstractN‐Substituted (3S,4S)‐ and (3R,4R)‐pyrrolidine‐3,4‐diols 9 and 10, respectively, were derived from (+)‐L‐ and (−)‐D‐tartaric acid, respectively. Compounds 9k, 9l, and 9m with the N‐substituents, BnNH(CH2)2, 4‐PhC6H4CH2NH(CH2)2 and 4‐ClC6H4CH2NH(CH2)2, respectively, showed modest inhibitory activities toward α‐D‐amyloglucosidases from Aspergillus niger and from Rhizopus mold (Table 1). Unexpectedly, several (3R,4R)‐pyrrolidine‐3,4‐diols 10 showed inhibitory activities toward α‐D‐mannosidases from almonds and from jack bean (Table 3). N‐Substitution by the NH2(CH2)2 group, i.e., 10g, led to the highest potency.