Solid-support based total synthesis and stereochemical correction of brunsvicamide A

Org Lett. 2008 Aug 7;10(15):3199-202. doi: 10.1021/ol801064d. Epub 2008 Jul 1.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Stereoisomerism

Substances

  • Peptides, Cyclic
  • brunsvicamide A