Facile synthesis of 2-alkyl substituted carbapenems via palladium-catalyzed cross-coupling reaction

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2589-2592

  Narukawa, Yukitoshi ^a   Nishi, Koichi ^a   Onoue, Hiroshi ^a  

^a SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAPENEM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029928211     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00377-2     Document Type: Article

References (20)

1. (a) imipenem: Leanza, W. J.; Wildonger, K. J.; Miller, T. W.; Christensen, B. G. J. Med. Chem. 1979, 22, 1435.
2. (b) panipenem: Miyadera, T.; Sugimura, Y.; Hashimoto, T.; Tanaka, T.; Iino, K.; Shibata, T.; Sugawara, S. J. Antibiot. 1983, 36, 1034.
3. (c) biapenem: Nagao, Y.; Nagase, Y.; Kumagai, T.; Matsunaga, H.; Abe, T.; Shimada, O.; Hayashi, T.; Inoue, Y. J. Org. Chem. 1992, 57, 4243.
4. (d) meropenem: Sunagawa, M.; Matsumura, H.; Inoue, T.; Fukasawa, M.; Kato, M. J. Antibiot. 1990, 43, 519.
5. For example, see: Fujimoto, K.; Iwano, Y.; Hirai, K. Bull. Chem. Soc. Jpn. 1986, 59, 1363. Recently, a new synthesis of 2-alkylcarbapenem was reported: Feigelson, G. B. Tetrahedron Lett., 1995, 36, 7407.
6. For example, see: Fujimoto, K.; Iwano, Y.; Hirai, K. Bull. Chem. Soc. Jpn. 1986, 59, 1363. Recently, a new synthesis of 2-alkylcarbapenem was reported: Feigelson, G. B. Tetrahedron Lett., 1995, 36, 7407.
7. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
8. Syntheses of 2-arylcarbapenems via Stille coupling-reaction and Suzuki coupling-reaction were reported: (a) Rano, T. A.; Greenlee, M. L.; DiNinno, F. P. Tetrahedron Lett. 1990, 31, 2853.
9. (b) Yasuda, N.; Xavier, L.; Rieger, D. L.; Li, Y.; DeCamp, A. E.; Dolling, U.-H. Tetrahedron Lett. 1993, 34, 3211.
10. Enol triflate PMB esters 5a,b were prepared in a similar way as described in literatures: (a) Ueda, Y.; Roberge, G.; Vinet, V. Can. J. Chem. 1984, 62, 2936.
11. (b) Fliri, H.; Mak, C.-P. J. Org. Chem. 1985, 50, 3438.
12. (c) Shin, D. H.; Baker, F.; Cama, L.; Christensen, B. G. Heterocycles, 1984, 27, 29.
13. (d) Uyeo, S.; Itani, H. Tetrahedron Lett. 1991, 32, 2143.
14. (e) Itani, H.; Uyeo, S. Synlett 1995, 213. These triflates 5 were prepared from diazo compounds just prior to use for the cross-coupling reactions.
15. 2O: C, 48.93; H, 7.33; N, 13.17. Found: C, 48.87; H, 7.03; N, 13.09.
16. 2 oxidation. Formation of trans-pyrrolidine isomer could not be detected.
17. Ohtani, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1984, 49, 5271.
18. 2. The less polar isomer 10 having S-configuration was converted into the final product 2b.
19. Preliminary in vitro antimicrobial assay against Gram-positive and Gram-negative bacteria revealed that these carbapenems showed comparable (3b) or reduced activity (1b, 2b, 4b) compared with that of their sulfur analogs 1a-4a, respectively.
20. Full details of olefin syntheses 7-9 and deprotection to final carbapenems 1b-4b will be reported in due course.