Stereoselective synthesis of highly functionalized 5- and 6-membered aminocyclitols starting with a readily available 2-azetidinone.

Stereoselective transformations of 4-vinyl-2-azetidinone derivative 4 into a variety of highly functionalized 6- and 5-membered carbocyclic compounds 7 and 9 were carried out using sequences involving sequential C1-N bond cleavage and Ru-catalyzed ring-closing metathesis. The derived carbocycles were further transformed into polyhydroxylated 6- and 5-membered aminocyclitols.