Practical synthesis of anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem L-742,728

Nobuyoshi Yasuda, Mark A. Huffman, Guo Jie Ho, Lyndon C. Xavier, Chunhua Yang, Khateeta M. Emerson, Fuh Rong Tsay, Yulan Li, Michael H. Kress, Dale L. Rieger, Sandor Karady, Paul Sohar, Newton L. Abramson, Ann E. DeCamp, David J. Mathre, Alan W. Douglas, Ulf H. Dolling, Edward J.J. Grabowski, Paul J. Reider

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Abstract

Anti-MRSA carbapenem, L-742,728, has been prepared in large quantity using the Suzuki-Miyaura cross-coupling as the key reaction. Three approaches have been examined by varying the coupling reaction between carbapenem nucleus A and side chains B, BC, and BCD, wherein BCD represents the fully elaborated side chain. The coupling of A with BCD offers the advantage of convergence and requires fewer chemical steps after installation of the thermally unstable carbapenem skeleton. This key reaction highlights the versatility and efficiency of the Suzuki-Miyaura reaction. This approach offers a general method for the preparation of the 3-aryl carbapenems, which possess strong antibacterial activity against resistant strains.

Original languageEnglish (US)
Pages (from-to)5438-5446
Number of pages9
JournalJournal of Organic Chemistry
Volume63
Issue number16
DOIs
StatePublished - Aug 7 1998
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Yasuda, N., Huffman, M. A., Ho, G. J., Xavier, L. C., Yang, C., Emerson, K. M., Tsay, F. R., Li, Y., Kress, M. H., Rieger, D. L., Karady, S., Sohar, P., Abramson, N. L., DeCamp, A. E., Mathre, D. J., Douglas, A. W., Dolling, U. H., Grabowski, E. J. J., & Reider, P. J. (1998). Practical synthesis of anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem L-742,728. Journal of Organic Chemistry, 63(16), 5438-5446. https://doi.org/10.1021/jo980381n