Asymmetric synthesis of (-)-incarvillateine employing an intramolecular alkylation via Rh-catalyzed olefinic C-H bond activation.
An asymmetric total synthesis of (-)-incarvillateine, a natural product having potent analgesic properties, has been achieved in 11 steps and 15.4% overall yield. The key step is a rhodium-catalyzed intramolecular alkylation of an olefinic C-H bond to set two stereocenters. Additionally, this transformation produces an exocyclic, tetrasubstituted alkene through which the bicyclic piperidine moiety can readily be accessed.
Tsai
Andy S
AS
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Bergman
Robert G
RG
Ellman
Jonathan A
JA
D000470:Alkaloids / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D039821:Monoterpenes / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000475:Alkenes; D039821:Monoterpenes; C400141:incarvillateine; D012238:Rhodium