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

Investor logo
Investor logo
Investor logo

Warning

This publication doesn't include Faculty of Arts. It includes Faculty of Science. Official publication website can be found on muni.cz.
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.
Related projects:

You are running an old browser version. We recommend updating your browser to its latest version.