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

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Authors

THARRA Prabhakara Rao MIKHAYLOV Andrey ŠVEJKAR Jiří GYSIN Marina HOBBIE Sven N. ŠVENDA Jakub

Year of publication 2022
Type Article in Periodical
Magazine / Source Angewandte Chemie International Edition
MU Faculty or unit

Faculty of Science

Citation
Web https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202116520
Doi http://dx.doi.org/10.1002/anie.202116520
Keywords Antibiotics; Natural Products; Organic Synthesis; Radical Chemistry; Ribosome Inhibitors
Description 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 alpha-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.
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