A Convenient Approach towards the Synthesis of ADMDP Type Iminosugars and Nojirimycin Derivatives from Sugar-Derived Lactams.

An efficient method for the synthesis of nojirimycin- and pyrrolidine-based iminosugar derivatives has been developed. The strategy is based on the partial reduction in sugar-derived lactams by Schwartz's reagent and tandem stereoselective nucleophilic addition of cyanide or a silyl enol ether dictated by Woerpel's or diffusion control models, which affords amino-modified iminosugars, such as ADMDP or higher nojirimycin derivatives.