title: Solid-support based total synthesis and stereochemical correction of brunsvicamide A.
abstract: A total synthesis of the cyanobacterial metabolite brunsvicamide A and the correction of its originally assigned stereochemistry are reported. Key elements were the construction of a urea building block, peptide elongation on solid phase, and on-resin cyclization of the peptide chain, with good overall yield. Detailed structural investigations uncovered that brunsvicamide A features a previously undetected d-lysine residue in its backbone, setting the foundation for all further investigations in this compound class.
authors.affiliation: TU Dortmund, Fakultät Chemie, Otto-Hahn-Str. 6, D-44221 Dortmund, Germany.
authors.forename: Thilo
authors.initials: T
authors.lastname: Walther
authors.forename: Hans-Dieter
authors.initials: HD
authors.lastname: Arndt
authors.forename: Herbert
authors.initials: H
authors.lastname: Waldmann
mesh_terms: D002851:Chromatography, High Pressure Liquid; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D010456:Peptides, Cyclic; C513364:brunsvicamide A