A convergent approach to huperzine A and analogues

Abstract

We describe a concise and convergent synthesis of (rac)-5-methoxy-6-azatricyclco[7.3.1.0^2,7]trideca-2(7),3,5,11-tetraen-13-ol, which has the basic ring system of huperzine A, a potent inhibitor of acetylcholinesterase. We also describe the synthesis of the novel system 5-methoxy-6-azatricyclo[7.2.2.0^2,7]trideca-2(7),3,5-trien-10-one and a series of related systems.