A facile synthesis of 7-amino-3-desacetoxycephalosporanic acid derivatives by indium-mediated reduction of 3-iodomethylcephems in aqueous media

Tetrahedron Letters

Volumn 41, Issue 20, 2000, Pages 3899-3901

  Chae, Hyungsun ^a   Cho, Sangwon ^a   Keum, Gyochang ^a   Kang, Soon Bang ^a   Pae, Ae Nim ^a   Kim, Youseung ^a  

^a Korea Institute of Science and Technology   (South Korea)

Author keywords

Cephalosporin; Dehalogenation; Halogens and compounds; Indium and compounds; Reactions in; Water

Indexed keywords

CEPHALOSPORANIC ACID DERIVATIVE; CEPHEM DERIVATIVE; INDIUM;

AQUEOUS SOLUTION; ARTICLE; DEHALOGENATION; ELECTROCHEMICAL ANALYSIS; ISOMERISM; REACTION ANALYSIS; REDUCTION; SYNTHESIS; TEMPERATURE;

EID: 0034697532     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00512-8     Document Type: Article

References (22)

1. Ryan, C. W.; Simon, R. L.; Heyningen, E. M. J. Med. Chem. 1969, 12, 310-313.
2. Dolfini, J. E.; Applegate, H. E.; Bach, G.; Basch, H.; Bernstein, J.; Schwatz, J.; Weisenborn, F. L. J. Med. Chem. 1969, 14, 117-119.
3. Dunn, G. L.; Hoover, J. R. E.; Berges, D. A.; Taggart, J. J.; Davis, L. D.; Dietz, E. M.; Jakas, D. R.; Yim, N.; Actor, P.; Uri, J. V.; Weisbach, J. A. J. Antibiotics 1976, 29, 65-80.
4. Ochiai, M.; Morimoto, A.; Matsushita, Y. DE 2715385, 1977; Chem. Abstr. 1977, 88, 37820.
5. Ochiai, M.; Morimoto, A.; Matsushita, Y. DE 2715385, 1977; Chem. Abstr. 1977, 88, 37820.
6. Mobashery, S.; Johnston, M. J. Org. Chem. 1986, 51, 4723-4726.
7. Stedman, R. J.; Swered, K.; Hoover, J. R. E. J. Med. Chem. 1964, 7, 117-119.
8. Torii, S.; Tanaka, H.; Ohshima, T.; Sasaoka, M. Bull. Chem. Soc. Jpn. 1986, 59, 3975-3976.
9. Morin, R. B.; Jackson, B. G.; Mueller, R. A.; Lavagnino, E. R.; Scanlon, W. B.; Andrews, S. L. J. Am. Chem. Soc. 1963, 86, 1896-1897.
10. Morin, R. B.; Jackson, B. G.; Mueller, R. A.; Lavagnino, E. R.; Scanlon, W. B.; Andrews, S. L. J. Am. Chem. Soc. 1969, 27, 1401-1407.
11. Chauvette, R. R.; Pennington, P. A.; Ryan, C. W.; Cooper, R. D. G.; Jose, F. L.; Wright, I. G.; Heyningen, E. M. V.; Huffman, G. W. J. Org. Chem. 1971, 36, 1259-1267.
12. Hashmi, A. S. K. J. Prakt. Chem. 1998, 340, 84-89.
13. Cintas, P. Synlett 1995, 1087-1096.
14. Lim, H. J.; Keum, G.; Kang, S. B.; Chung, B. Y.; Kim, Y. Tetrahedron Lett. 1998, 39, 4367-4368.
15. Lim, H. J.; Keum, G.; Kang, S. B.; Chung, B. Y.; Kim, Y. Tetrahedron Lett. 1999, 40, 1547-1550.
16. Araki, S.; Shimizu, T.; Johar, P. S.; Jin, S.; Butsugan, Y. J. Org. Chem. 1991, 56, 2538-2541.
17. Sugiyama, I.; Komatsu, Y.; Yamauchi, H. J. Antibiot. 1992, 45, 103-112.
18. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1991.
19. Miyake, A.; Yoshimura, Y.; Yamaoka, M. J. Antibiot. 1992, 45, 709-720.
20. Ochiai, M.; Aki, O.; Morimoto, A.; Okada, T.; Shinozaki, K.; Asahi, Y. Tetrahedron Lett. 1972, 23, 2341-2344.
21. Chauvette, R. R.; Pennington, P. A. J. Org. Chem. 1973, 38, 2994-2999.
22. Ono, A.; Fusimoto, A.; Ueno, M. Synth. Commun. 1986, 16, 653-657.