OBERHEIDE , Ansgar

Marine bacteria produce highly cytotoxic polyheterocyclic cyclopeptide natural products by ribosomal peptide biosynthesis. Among them, urukthapelstatin A features a chain of five 2,4′-connected azole rings within a cyclo-octapeptide framework. We report a novel synthesis design that uses only α-amino acids as starting materials that leads to an...

Analogs of the natural product urukthapelstatin A that belongs to the rare family of polyazole cyclopeptides were synthesized and their cytotoxic activities were determined to gather data toward structure-activity relationships. Crucial steps within the convergent syntheses were a macrothiolacton-ization and a subsequent aza-Wittig reaction to...