Asymmetric synthesis of the carbapenam core from serine

Journal of Organic Chemistry

Volumn 68, Issue 1, 2003, Pages 187-190

  Hart, Barry P ^a   Verma, Sharad K ^a   Rapoport, Henry ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSPECIFIC SYNTHESIS;

SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

BETA LACTAM ANTIBIOTIC; CARBAPENEM DERIVATIVE; PYRROLIDINE DERIVATIVE; SERINE; SULFONAMIDE; THIENAMYCIN;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; FERMENTATION TECHNIQUE; STEREOSPECIFICITY;

CARBAPENEMS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRROLIDINES; SERINE; STEREOISOMERISM;

EID: 0037428041     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026499s     Document Type: Article

References (22)

1. Present address: Bayer Pharmaceuticals, Department of Chemistry, 400 Morgan Lane, West Haven, CT 06516.
2. (a) Overviews of β-lactam antibiotics: The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie Academic & Professional: New York, 1992. (b) The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Press: New York, 1993. (c) Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vols. 1-3. (d) Samarendra, C. I.; Maiti, N.; Micetich, R. G.; Daneshtalab, M.; Atchison, K.; Phillips, O. A.; Kunugita, C. J. Antibiot. 1994, 47, 1030.
3. (a) Overviews of β-lactam antibiotics: The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie Academic & Professional: New York, 1992. (b) The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Press: New York, 1993. (c) Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vols. 1-3. (d) Samarendra, C. I.; Maiti, N.; Micetich, R. G.; Daneshtalab, M.; Atchison, K.; Phillips, O. A.; Kunugita, C. J. Antibiot. 1994, 47, 1030.
4. (a) Overviews of β-lactam antibiotics: The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie Academic & Professional: New York, 1992. (b) The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Press: New York, 1993. (c) Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vols. 1-3. (d) Samarendra, C. I.; Maiti, N.; Micetich, R. G.; Daneshtalab, M.; Atchison, K.; Phillips, O. A.; Kunugita, C. J. Antibiot. 1994, 47, 1030.
5. (a) Overviews of β-lactam antibiotics: The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie Academic & Professional: New York, 1992. (b) The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Press: New York, 1993. (c) Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vols. 1-3. (d) Samarendra, C. I.; Maiti, N.; Micetich, R. G.; Daneshtalab, M.; Atchison, K.; Phillips, O. A.; Kunugita, C. J. Antibiot. 1994, 47, 1030.
6. Kahan, J. S.; Kahan, F.; Goegelman, R.; Currie, S. A.; Jackson, M.; Stapley, E. O.; Miller, T. W.; Miller, A. K.; Hendlin, D.; Mochales, S.; Hernandez, S.; Woodruff, H. B.; Birnbaum, J. J. Antibiot. 1979, 32, 1.
7. (a) Ratcliffe, R. W.; Albers-Schonberg, G. The Chemistry of Thienamycin and Other Carbapenem Antibiotics. In Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vol. 2, p 227.
8. (b) Kametani, T.; Fukumoto, K.; Ihara, M. Heterocycles 1982, 17, 463.
9. (c) Albers-Schonberg, G.; Arison, B. H.; Hensens, O. D.; Hirshfield, J.; Hoogsteen, K.; Kaczka, E. A.; Rhodes, R. E.; Kahan, J. S.; Kahan, F. M.; Ratcliffe, R. W.; Walton, E.; Ruswinkle, L. J.; Morin, R. B.; Christensen, B. G. J. Am. Chem. Soc. 1978, 100, 6491.
10. For a review on the state of carbapenem antibiotics, see: (a) Coulton, S.; E. Hunt. In Progress in Medicinal Chemistry; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier: New York, 1996; Vol. 33, pp 99-145. (b) Kim, O.; Fung-Tomc, J. Expert Opin. Ther. Pat. 2001, 11, 8. (c) Bonfiglio, G.; Russo, G.; Nicoletti, G. Expert Opin. Invest. Drugs 2002, 11, 4.
11. For a review on the state of carbapenem antibiotics, see: (a) Coulton, S.; E. Hunt. In Progress in Medicinal Chemistry; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier: New York, 1996; Vol. 33, pp 99-145. (b) Kim, O.; Fung-Tomc, J. Expert Opin. Ther. Pat. 2001, 11, 8. (c) Bonfiglio, G.; Russo, G.; Nicoletti, G. Expert Opin. Invest. Drugs 2002, 11, 4.
12. For a review on the state of carbapenem antibiotics, see: (a) Coulton, S.; E. Hunt. In Progress in Medicinal Chemistry; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier: New York, 1996; Vol. 33, pp 99-145. (b) Kim, O.; Fung-Tomc, J. Expert Opin. Ther. Pat. 2001, 11, 8. (c) Bonfiglio, G.; Russo, G.; Nicoletti, G. Expert Opin. Invest. Drugs 2002, 11, 4.
13. (a) Hart, B. P.; Rapoport, H. J. Org. Chem. 1999, 64, 2050.
14. (b) Verma, S. K.; Atanes, M. N.; Busto, J. H.; Thai, D. L.; Rapoport, H. J. Org. Chem. 2002, 67, 1314.
15. (c) Folmer, J. J.; Acero, C.; Thai, D. L.L.; Rapoport, H. J. Org. Chem. 1998, 63, 8170.
16. (a) Berks, A. H. Tetrahedron 1996, 52, 331.
17. (b) Humphrey, G.; Miller, R. A.; Pye, P. J.; Rossen, K.; Reamer, R. A.; Maliakal, A.; Ceglia, S. S.; Grabowski, E. J. J.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1999, 121, 11261 and references therein.
18. (a) Tanaka, H.; Sakagami, H.; Ogasawara, K. Tetrahedron Lett. 2002, 43, 93.
19. (b) Miyashita, M.; Chida, N.; Yoshikoshi, A. J. Chem. Soc., Chem. Commun. 1984, 195.
20. Sodium naphthalenide was generated as described by: (a) Bergmeir, S. C.; Seth, P. P. Tetrahedron Lett. 1999, 40, 6181. (b) Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 5311.
21. Sodium naphthalenide was generated as described by: (a) Bergmeir, S. C.; Seth, P. P. Tetrahedron Lett. 1999, 40, 6181. (b) Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 5311.
22. Kawai, A.; Hara, T.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1988, 29, 6331.