Oxazatricyclic noradamantanes: stereocontrolled synthesis of functionalized scopolines, related cage molecules, and drug leads.

Scopolines 4 and the noradamantane scaffold are accessible from 8-oxabicyclo[3.2.1]oct-6-en-3-ones such as 6 by a concise route involving introduction of an axial amino nitrogen at C3, epoxidation, and cyclization. The resulting cage molecules are versatile drug leads.