Addition of metallo enolates to chiral 1-acylpyridinium salts: total synthesis of (+)-cannabisativine.
[formula: see text] A novel route to the first asymmetric synthesis of (+)-cannabisativine (1) is described. The total synthesis of 1 was accomplished with a high degree of regio- and stereoselectivity in 19 steps and 9% overall yield.
Kuethe
J T
JT
Department of Chemistry, North Carolina State University, Raleigh 27695-8204, USA.
Comins
D L
DL
D002186:Cannabinoids / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds; D011726:Pyridinium Compounds; D013237:Stereoisomerism
D002186:Cannabinoids; D009942:Organometallic Compounds; D011726:Pyridinium Compounds; C012801:cannabisativine