title: Asymmetric synthesis of (-)-incarvillateine employing an intramolecular alkylation via Rh-catalyzed olefinic C-H bond activation.
abstract: 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.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Andy S
authors.initials: AS
authors.lastname: Tsai
authors.forename: Robert G
authors.initials: RG
authors.lastname: Bergman
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D039821:Monoterpenes / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000475:Alkenes; D039821:Monoterpenes; C400141:incarvillateine; D012238:Rhodium