ol8b03940_si_001.pdf (5.51 MB)
Solid-Phase-Based Total Synthesis and Stereochemical Assignment of the Cryptic Natural Product Aurantizolicin
journal contribution
posted on 2019-01-11, 20:47 authored by Ansgar Oberheide, Sebastian Pflanze, Pierre Stallforth, Hans-Dieter ArndtThe total synthesis
and stereochemical assignment of the polyazole
cyclopeptide aurantizolicin was achieved by connecting the solution
synthesis of building blocks with solid-phase peptide synthesis. Macrothiolactonization
and an aza-Wittig reaction provided the natural product
macrocycle in high yield as well as key stereoisomers. NMR comparison
as well as isolation of the natural product from the producer organism Streptomyces aurantiacus confirmed the presence and
sequence of one l-Ile and one d-allo-Ile residue in aurantizolicin.