Expeditious Synthesis of a Common Intermediate of L-1-Deoxyallonojirimycin and L-1-Deoxymannojirimycin.

The expeditious synthesis of a common intermediate of L-1- deoxyallonojirimycin (L-allo-DNJ) and L- 1 -deoxymannojiri-mycin (L-manno-DNJ) is reported. This intermediate is obtained in highly diastereo- and enantioselectivity with 38.4% overall yield in six steps involving the unprecedented ring-closing metathesis of a tert-butylsulfinyl allylamine as the key step. [ABSTRACT FROM AUTHOR]