title: Nine-step enantioselective total synthesis of (-)-vincorine.
abstract: A concise and highly enantioselective total synthesis of the akuammiline alkaloid (-)-vincorine has been accomplished. A key element of the synthesis is a stereoselective organocatalytic Diels-Alder, iminium cyclization cascade sequence, which serves to construct the tetracyclic alkaloid core architecture in one step from simple achiral precursors. The challenging seven-membered azepanyl ring system is installed by way of a single electron-mediated cyclization event initiated from an acyl telluride precursor. The total synthesis of (-)-vincorine is achieved in nine steps and 9% overall yield from commercially available starting materials.
authors.affiliation: Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA.
authors.forename: Benjamin D
authors.initials: BD
authors.lastname: Horning
authors.forename: David W C
authors.initials: DW
authors.lastname: MacMillan
mesh_terms: D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013237:Stereoisomerism; D014748:Vinca Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D014961:X-Ray Diffraction
chemical_list: D007202:Indicators and Reagents; D014748:Vinca Alkaloids; C543267:vincorine