10.1021/acs.orglett.8b03940.s001
Ansgar Oberheide
Ansgar
Oberheide
Sebastian Pflanze
Sebastian
Pflanze
Pierre Stallforth
Pierre
Stallforth
Hans-Dieter Arndt
Hans-Dieter
Arndt
Solid-Phase-Based Total Synthesis and Stereochemical
Assignment of the Cryptic Natural Product Aurantizolicin
American Chemical Society
2019
building blocks
stereochemical assignment
Ile residue
NMR comparison
producer organism Streptomyces aurantiacus
Wittig reaction
Stereochemical Assignment
product macrocycle
solution synthesis
polyazole cyclopeptide aurantizolicin
Cryptic Natural Product Aurantizolicin
solid-phase peptide synthesis
2019-01-11 20:47:44
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Solid-Phase-Based_Total_Synthesis_and_Stereochemical_Assignment_of_the_Cryptic_Natural_Product_Aurantizolicin/7579910
The 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 <i>aza</i>-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-<i>allo</i>-Ile residue in aurantizolicin.