Solid-support based total synthesis and stereochemical correction of brunsvicamide A.
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.
Walther
Thilo
T
TU Dortmund, Fakultät Chemie, Otto-Hahn-Str. 6, D-44221 Dortmund, Germany.
Arndt
Hans-Dieter
HD
Waldmann
Herbert
H
D002851:Chromatography, High Pressure Liquid; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010456:Peptides, Cyclic; C513364:brunsvicamide A