A total synthesis of (+/-)-alpha-cyclopiazonic acid using a cationic cascade.
The indolic terpene alkaloid alpha-cyclopiazonic acid has been prepared in 11 steps from indole-4-methanol; the key step is a carbocationic cascade, terminated by a 4-nitrosulfonamide group and initiated by benzylic carbocation formation directly from the intermediate , which gives the tetracyclic product in 74% yield.
Haskins
Charlotte M
CM
School of Chemistry, Cardiff University, Main Building, UK.
Knight
David W
DW
D002412:Cations; D007211:Indoles / Q000138:chemical synthesis*
D002412:Cations; D007211:Indoles; C000543:cyclopiazonic acid