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.