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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