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Oberheide A, Pflanze S, Stallforth P, et al. Solid-Phase-Based Total Synthesis and Stereochemical Assignment of the Cryptic Natural Product Aurantizolicin. Org Lett. 2019;21(3):729-732doi: 10.1021/acs.orglett.8b03940.
Oberheide, A., Pflanze, S., Stallforth, P., & Arndt, H. D. (2019). Solid-Phase-Based Total Synthesis and Stereochemical Assignment of the Cryptic Natural Product Aurantizolicin. Organic letters, 21(3), 729-732. https://doi.org/10.1021/acs.orglett.8b03940
Oberheide, Ansgar, et al. "Solid-Phase-Based Total Synthesis and Stereochemical Assignment of the Cryptic Natural Product Aurantizolicin." Organic letters vol. 21,3 (2019): 729-732. doi: https://doi.org/10.1021/acs.orglett.8b03940
Oberheide A, Pflanze S, Stallforth P, Arndt HD. Solid-Phase-Based Total Synthesis and Stereochemical Assignment of the Cryptic Natural Product Aurantizolicin. Org Lett. 2019 Feb 01;21(3):729-732. doi: 10.1021/acs.orglett.8b03940. Epub 2019 Jan 11. PMID: 30633530.
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Org Lett. 2019 Feb 01;21(3):729-732. doi: 10.1021/acs.orglett.8b03940. Epub 2019 Jan 11.

Solid-Phase-Based Total Synthesis and Stereochemical Assignment of the Cryptic Natural Product Aurantizolicin.

Organic letters

Ansgar Oberheide, Sebastian Pflanze, Pierre Stallforth, Hans-Dieter Arndt

Affiliations

  1. Friedrich-Schiller-Universität , Institut für Organische und Makromolekulare Chemie , Humboldtstr. 10 , D-07743 Jena , Germany.
  2. Leibniz Institute for Natural Product Research and Infection Biology, Hans Knöll Institute (HKI) , Chemistry of Microbial Communication , Beutenbergstr. 11A , D-07745 Jena , Germany.

PMID: 30633530 DOI: 10.1021/acs.orglett.8b03940

Abstract

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 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.

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