| THARRA, Prabhakara Rao, Andrey MIKHAYLOV, Jiří ŠVEJKAR, Marina GYSIN, Sven N. HOBBIE and Jakub ŠVENDA. Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis. Angewandte Chemie International Edition. Wiley VCHGmbH, 2022, vol. 61, No 17, p. 1-6. ISSN 1433-7851. Available from: https://dx.doi.org/10.1002/anie.202116520. |
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@article{1850761,
author = {Tharra, Prabhakara Rao and Mikhaylov, Andrey and Švejkar, Jiří and Gysin, Marina and Hobbie, Sven N. and Švenda, Jakub},
article_number = {17},
doi = {http://dx.doi.org/10.1002/anie.202116520},
keywords = {Antibiotics; Natural Products; Organic Synthesis; Radical Chemistry; Ribosome Inhibitors},
language = {eng},
issn = {1433-7851},
journal = {Angewandte Chemie International Edition},
title = {Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis},
url = {https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202116520},
volume = {61},
year = {2022}
}
TY - JOUR
ID - 1850761
AU - Tharra, Prabhakara Rao - Mikhaylov, Andrey - Švejkar, Jiří - Gysin, Marina - Hobbie, Sven N. - Švenda, Jakub
PY - 2022
TI - Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis
JF - Angewandte Chemie International Edition
VL - 61
IS - 17
SP - 1-6
EP - 1-6
PB - Wiley VCHGmbH
SN - 14337851
KW - Antibiotics
KW - Natural Products
KW - Organic Synthesis
KW - Radical Chemistry
KW - Ribosome Inhibitors
UR - https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202116520
N2 - 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.
ER -
THARRA, Prabhakara Rao, Andrey MIKHAYLOV, Jiří ŠVEJKAR, Marina GYSIN, Sven N. HOBBIE and Jakub ŠVENDA. Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis. \textit{Angewandte Chemie International Edition}. Wiley VCHGmbH, 2022, vol.~61, No~17, p.~1-6. ISSN~1433-7851. Available from: https://dx.doi.org/10.1002/anie.202116520.
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