A convergent approach to huperzine A and analogues.
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.
Kelly
Seán A
SA
School of Chemistry, Queen's University Belfast, Stranmillis Road, Belfast BT9 5AG, Northern Ireland.
Foricher
Yann
Y
Mann
John
J
Bentley
Jonathan M
JM
D000470:Alkaloids; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry; D007536:Isomerism; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D002800:Cholinesterase Inhibitors; D003512:Cyclohexanones; D012717:Sesquiterpenes; C050426:huperzine A