2. Academic Validation
  3. Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis

Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis

  • Angew Chem Int Ed Engl. 2022 Apr 19;61(17):e202116520. doi: 10.1002/anie.202116520.
Prabhakara R Tharra 1 2,  Andrey A Mikhaylov 1 2,  Jiří Švejkar 1,  Marina Gysin 3,  Sven N Hobbie 3,  Jakub Švenda 1 2
Affiliations

Affiliations

  • 1 Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, Brno, 625 00, Czech Republic.
  • 2 International Clinical Research Center, St. Anne's University Hospital, Pekařská 53, Brno, 656 91, Czech Republic.
  • 3 Institute of Medical Microbiology, University of Zürich, Gloriastrasse 30, Zürich, 8006, Switzerland.
PMID: 35167723 DOI: 10.1002/anie.202116520
Abstract

We report a concise synthesis of the naturally occurring protein synthesis inhibitor (+)-actinobolin (1). The densely functionalized and stereochemically complex molecular structure of 1 was assembled from (-)-quinic acid, L-threonine, and L-alanine as the principal components. Our route is based around a convergent strategy that features conjugate addition of an α-amino radical in the key fragment-coupling step. The dramatically simplified synthesis of (+)-actinobolin proceeding in 9 steps with 18 % overall yield has practical implications for analog preparation, as demonstrated herein.

Keywords

Antibiotics; Natural Products; Organic Synthesis; Radical Chemistry; Ribosome Inhibitors.

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