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

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5438-5446

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

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAPENEM DERIVATIVE; L 742728; METICILLIN; UNCLASSIFIED DRUG;

ANTIBIOTIC RESISTANCE; ARTICLE; BACTERICIDAL ACTIVITY; DRUG SYNTHESIS; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS INFECTION;

EID: 7344236839     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980381n     Document Type: Article

References (32)

1. (1)(a) Methicillin Resistant Staphylococcus aureus; University of Tokyo Press: Tokyo, 1986.
2. (b) Brumfitt, W.; Hamilton-Miller, J. N. Eng. J. Med. 1989, 320, 1188.
3. McDonald, O. J. Med. J. Australia 1982, 1, 445.
4. Very recently, vancomycin resistant MRSA has been reported. Michel, M.; Gutmann, L. Lancet 1997, 349, 1901.
5. Noble, W. C.; Virani, Z.; Cree, R. G. A. FEMS Microb. Lett. 1992, 93, 195.
6. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
7. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
8. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
9. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
10. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
11. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
12. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
13. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
14. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
15. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
16. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
17. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
18. Previously, we reported this class of carbapenem as 2-aryl carbapenem based on the traditional numbering system in β-lactam chemistry. In this report, we use the IUPAC numbering system as depicted in L-742,728 (1). (a) Greenlee, M. L.; Cama, L. D.; DiNinno, F. P.; Heck, J. V. U.S. Pat. 5034384, 1991. (b) DiNinno, F.; Dykstra, K. D.; Greenlee, M. L.; Rano, T. A.; Guthikonda, R. N.; Schmitt, S. M.; Meurer, L. C.; Cama, L. D.; Sasor, M. F.; Laub, J. B.; Rouen, G. P.; Lee, W.; Muthard, D. A.; Hammond, M. L.; Heck, J. V.; Salzmann, T. N.; Kahan, J. S.; Huber, J. L.; Sundelof, J. G.; Dorso, K.; Kohler, J.; Gerkens, L.; Pelak, B.; St. Rose, E.; Jackson, J. J.; Hajdu, R.; Kropp, H.; Hammond, G. G.; Overbye, K. M.; Silver, L. L. The 4th International Conference on Chemical Synthesis of Antibiotics and Related Microbial Products, Nashville, IN, September 1994. (c) Sasor, M. F.; Cama, L. D.; Greenlee, M. L.; DiNinno, F.; Heck, J. V. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 50, Orlando, FL, October 1994. (d) Huber, J. L.; Dorso, K.; Gerckens, L.; St. Rose, E.; Kohler, J.; Dufresne, S.; Kahan, J.; Shungu, D.; Kropp, H. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 54, Orlando, FL, October 1994. (e) Rylander, M.; Rollof, J.; Norrby, S. R. The 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, Paper #F 56, Orlando, FL, October 1994. (f) Dykstra, K. D.; DiNinno, F. The 6th Symposium on the Latest Trends in Organic Synthesis, Blacksburg, VA, October 1994. (g) Meurer, L. C.; Guthikonda, R. N.; Huber, J. L.; DiNinno, F. BioMed. Chem. Lett. 1995, 5, 767. (h) DiNinno, F.; Muthard, D. A.; Salzmann, T. N.; Huber J.; Kahan, J.; Kropp, H. BioMed. Chem. Lett. 1995, 5, 945. (i) Laub, J. B.; Greenlee, M. L.; DiNinno, F.; Huber, J. L.; Sundelof, J. G. The 210th National Meeting of the American Chemical Society, Abstract #MEDI 210, Chicago, IL, August 1995. (j) Chambers, H. F. Antimicrob. Agents Chemother. 1995, 39, 426. (k) Rylander, M.; Rollof, J.; Jacobsson, K.; Norrby, S. R. Antimicrob. Agents Chemother. 1995, 39, 1178. (l) Norby, S. R. Antimicrob. Therapy II 1995, 79, 745. (m) Yasuda, N. 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, HI, December 1995.
19. (a) Greenlee, M. L.; DiNinno, F.; Hammond, M. L. U.S. Pat. 5,451,579, 1995.
20. (b) Greenlee, M. L.; Laub, J. B.; Rouen, G. P.; DiNinno, F.; Cama, L. D.; Hammond, M. L.; Huber, J. L.; Sundelof, J. G.; Hammond, G. G. The 211th National Meeting of the American Chemical Society, Abstract #MEDI0178, New Orleans, LA, March 1996.
21. Compound 2 is readily available from (2R)-[(3S,4S)-3-[(1R)-tertbutyldimethylsilyloxyethyl]azetidinone-4-yl]propionic acid, which is now commercially available from Kanegafuchi, Japan, Nippon Soda, Japan, and Takasago, Japan. For recent preparation of the propionic acid; see: Jones, D. K.; Liotta, D. C.; Choi, W.-B.; Volante, R. P.; Reider, P. J. Shinkai, I.; Churchill, H. R. O.; Lynch, J. E. J. Org. Chem. 1994, 59, 3749 and references therein.
22. Rano, T. A.; Greenlee, M. L.; DiNinno, F. Tetrahedron Lett. 1990, 31, 2853 and references therein.
23. (a) Yasuda, N.; Xavier, L.; Rieger, D. L.; Li, Y.; DeCamp, A. E.; Jolling, U.-H. Tetrahedron Lett. 1993, 34, 3211.
24. (b) Narukawa, Y.; Nishi, K.; Onoue, H. Tetrahedron 1997, 53, 539 and references therein.
25. Douglas, A. W.; Abramson, N. L.; Houpis, I. N.; Karady, S.; Molina, A.; Xavier, L. C.; Yasuda, N. Tetrahedron Lett. 1994, 35, 6807 and references therein.
26. Karady, S.; Abramson, N. L.; Dolling. U.-H.; Douglas, A. W.; McManemin G. J.; Marcune, B. J. Am. Chem. Soc. 1995, 117, 5425.
27. Purchased from Aldrich Co. Ltd.
28. Liu, T. M.-H.; Lynch, J. E.; Volante, R. P. U.S. Pat. 5,493,018, 1996.
29. Silylation of the boronic acid 14 proved not to be a trivial task. The slow addition of 14 to a solution of BSA in THF at 40 °C was required to prevent formation of oligomeric boronic esters (a), which would give 27 after the coupling and workup. equation presented
30. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
31. Trademark of Mitsubishi Chemical Co. Ltd.
32. 2,2′-Azobis(2,4-dimethylvaleronitrile). Trademark of E. I. Du Pont De Nemours & Co. Inc.