A concise and convergent (formal) total synthesis of huperzine A.
The first convergent synthesis of the tricyclic skeleton of huperzine A is described and includes, as the key step, an efficient regioselective intramolecular Heck reaction of 2-(tert-butyldimethylsilyloxymethyl)-6-(2-methoxy-5-bromopyridin-6-yl)methylcyclohex-2-enol.
Lucey
Cathal
C
School of Chemistry, Queen's University Belfast, Stranmillis Road, Belfast, BT9 5AG, UK.
Kelly
Sean A
SA
Mann
John
J
D000470:Alkaloids; D002625:Chemistry, Organic / Q000379:methods*; D002626:Chemistry, Pharmaceutical / Q000379:methods; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D006868:Hydrolysis; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism
D000470:Alkaloids; D004791:Enzyme Inhibitors; D007659:Ketones; D012717:Sesquiterpenes; D012997:Solvents; C050426:huperzine A