Synthesis of Acidiphilamide A–C: Secondary Metabolites from the Genus Streptacidiphilus

Abstract

We describe the efficient total syntheses of naturally occurring tripeptides acidiphilamides A–C and epi-acidiphilamides A–C, which were prepared from commercially available l-phenyl alanine using hexafluorophosphate azabenzotriazole tetramethyl uronium (HATU) as peptide coupling reagent. The structures of the natural acidiphilamides A, B and C were characterized by NMR, MS and SOR data, which match those of natural products, whereas the structures of epi-acidiphilamides A, B and C were confirmed by 2D NMR studies.

Keywords

• total synthesis
• natural products
• acidiphilamides
• epi-acidiphilamides
• structural elucidation
• amide coupling reagents