title: Organocatalytic enantioselective total synthesis of (-)-arboricine.
abstract: The tetracyclic indole alkaloid (-)-arboricine has been prepared using an asymmetric organocatalytic Pictet-Spengler reaction as the key step followed by a diastereoselective Pd-catalyzed iodoalkene/enolate cyclization. The absolute stereochemistry was unequivocally proven by X-ray crystallographic analysis and appeared to be opposite to the published structure in the original paper.
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS, Amsterdam, The Netherlands.
authors.forename: Martin J
authors.initials: MJ
authors.lastname: Wanner
authors.forename: Rowan N A
authors.initials: RN
authors.lastname: Boots
authors.forename: Bram
authors.initials: B
authors.lastname: Eradus
authors.forename: René
authors.initials: R
authors.lastname: de Gelder
authors.forename: Jan H
authors.initials: JH
authors.lastname: van Maarseveen
authors.forename: Henk
authors.initials: H
authors.lastname: Hiemstra
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; C544042:arboricine