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

N Yasuda, MA Huffman, GJ Ho, LC Xavier…

Index: Yasuda, Nobuyoshi; Huffman, Mark A.; Ho, Guo-Jie; Xavier, Lyndon C.; Yang, Chunhua; Emerson, Khateeta M.; Tsay, Fuh-Rong; Li, Yulan; Kress, Michael H.; Rieger, Dale L.; Karady, Sandor; Sohar, Paul; Abramson, Newton L.; DeCamp, Ann E.; Mathre, David J.; Douglas, Alan W.; Dolling, Ulf-H.; Grabowski, Edward J. J.; Reider, Paul J. Journal of Organic Chemistry, 1998 , vol. 63, # 16 p. 5438 - 5446

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Citation Number: 32

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 ...