A highly refined version of the α-keto ester based carbapenem synthesis: The total synthesis of meropenem

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7035-7038

  Prashad, Amar S ^a   Vlahos, Nancy ^a   Fabio, Paul ^a   Feigelson, Gregg B ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAPENEM;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS;

EID: 0032563831     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01523-8     Document Type: Article

References (10)

1. 1. a) Feigelson, G. B. Tetrahedron Lett. 1995, 36, 7407.
2. b) Ziegler, C. B.; Curran, W. V.; Feigelson, G. B.; Bitha, P.; Fabio, P.; Strohmeyer, T.; Short, K.; Lin, Y-I Tetrahedron 1994, 50, 12085.
3. c) Feigelson, G. B. Tetrahedron Lett. 1993, 34, 4747.
4. 2. The original method for preparing meropenem is described in Sunagawa, M.; Matsumura, H.; Inoue, T.; Fukasawa, M.; Kato, M. J. Antibiotics 1990, 43, 519.
5. 3. For a review of meropenem's microbiological properties see: a) Fish, D. N.; Singletary, T. J. Pharmacotherapy 1997, 17, 644.
6. b) Blumer, J. L.; Int. J. Antimicrob. Agents 1997, 8, 73.
7. 3N in DMF.
8. 3) δ 8.22 (d, 4H), 7.64 (d, 2H), 7.51 (d, 1H), 7.43 (d, 1H), 5.49 (d, 1H), 5.24 (d, 1H), 5.20 (br s, 2H), 4.73 (m, 1H), 4.25 (m, 2H), 3.67 (m. 1H), 3.52 (m, 1H), 3.38 (m, 1H), 3.26 (m, 1H), 3.10, 2.98, 2.97, 2.95 (4s, 6H), 2.72 (1H, m), 1.93 (m, 1H), 1.36 (d, 3H), 1.25 (d, 3H).
9. 6. Prepared as described in Brands, K. M. J.; Marchesini, G.; Williams, J. M.; Dolling, U.-H.; Reider, P. J. Tetrahedron Lett. 1996, 37, 2919.
10. +) 384.1583.