title: Directed Synthesis of All Four Pure Stereoisomers of the N,C-Coupled Naphthylisoquinoline Alkaloid Ancistrocladinium A.
abstract: The first preparation of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A and its likewise naturally occurring minor atropisomer, in an atropisomerically pure form, is described. The synthesis succeeded by resolution of the already rotationally hindered, and thus atropo-diastereomeric acetamide precursors, which were then, without major loss of stereochemical information, cyclized to the respective target molecules. The strategy was applied to the first synthesis of the regioisomeric product ancistrocladinium D, likewise in a stereochemically pure form.
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Raina
authors.initials: R
authors.lastname: Seupel
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Barbara
authors.initials: B
authors.lastname: Hertlein-Amslinger
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Tanja
authors.initials: T
authors.lastname: Gulder
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Philipp
authors.initials: P
authors.lastname: Stawski
authors.affiliation: Swiss Tropical and Public Health Institute , Socinstrasse 57, CH-4002 Basel, Switzerland.|University of Basel , Petersplatz 1, CH-4003 Basel, Switzerland.
authors.forename: Marcel
authors.initials: M
authors.lastname: Kaiser
authors.affiliation: Swiss Tropical and Public Health Institute , Socinstrasse 57, CH-4002 Basel, Switzerland.|University of Basel , Petersplatz 1, CH-4003 Basel, Switzerland.
authors.forename: Reto
authors.initials: R
authors.lastname: Brun
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Gerhard
authors.identifier: 0000-0002-3583-5935
authors.initials: G
authors.lastname: Bringmann