title: Diastereodivergent Reverse Prenylation of Indole and Tryptophan Derivatives: Total Synthesis of Amauromine, Novoamauromine, and epi-Amauromine.
abstract: A regio- and stereoselective reverse prenylation of indole and tryptophan derivatives is presented. All four possible stereoisomers are accessible through this iridium-catalyzed reaction. The stereoselectivity is controlled by a chiral phosphoramidite ligand in combination with an achiral borane additive and can be switched by changing the nature of the borane. One enantiomer of the ligand is thus sufficient to prepare all possible isomers. The synthetic potential of this method was demonstrated by a short total synthesis of amauromine and its two natural diastereomers.
authors.affiliation: Fachbereich Chemie, Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King Platz 6, 20146, Hamburg, Germany.
authors.forename: Jonas M
authors.initials: JM
authors.lastname: Müller
authors.affiliation: Fachbereich Chemie, Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King Platz 6, 20146, Hamburg, Germany. stark@chemie.uni-hamburg.de.
authors.forename: Christian B W
authors.initials: CB
authors.lastname: Stark
keywords: alkaloids; diastereodivergent reactions; iridium; prenylation; total synthesis