A convergent approach to huperzine A and analogues

Org Biomol Chem. 2003 Aug 21;1(16):2865-76. doi: 10.1039/b305869g.

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.

MeSH terms

  • Alkaloids
  • Cholinesterase Inhibitors / chemical synthesis
  • Cyclization
  • Cyclohexanones / chemistry
  • Isomerism
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry

Substances

  • Alkaloids
  • Cholinesterase Inhibitors
  • Cyclohexanones
  • Sesquiterpenes
  • huperzine A