A formal synthesis of althiomycin

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 13, 1996, Pages 1543-1546

  Toogood, Peter L ^a   Hollenbeck, Jessica J ^a   Lam, Huong M ^a   Li, Li ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALTHIOMYCIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL INFECTION; DRUG MECHANISM; DRUG SYNTHESIS; PROKARYOTE; PROTEIN SYNTHESIS;

BACTERIA (MICROORGANISMS); PROKARYOTA;

EID: 0030576312     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00270-3     Document Type: Article

References (22)

1. 1. (a) Yaraaguchi, H.; Nakaya, Y.; Tawara, K.; Maeda, K.; Takeuchi, T.; Umezawa, H. J. Antibiot. Ser. A 1957, 10, 195.
2. (b) Nakamura, H.; Iitaka, Y.; Sakakibara, H.; Umezawa, H. J. Antibiot. 1974, 27, 894.
3. (c) Sakakibara, H.; Naganawa, H.; Ohno, M.; Maeda, K.; Umezawa, H. J. Antibiot. 1974, 27, 897.
4. (d) Kunze, B.; Reichenbach, H.; Augustiniak, H.; Höfle, G. J. Antibiot. 1983, 35, 635.
5. 2. Fujimoto, H.; Kinoshita, T.; Suzuki, H.; Umezawa, H. J. Antibiot. 1970, 23, 271.
6. 3. Pestka, S; Brot, N. J. Biol. Chem. 1971, 246, 7715.
7. 4. Burns, D. J.; Cundliffe, E. Eur. J. Biochem. 1973, 37, 570.
8. 5. (a) Kirst, H.; Szymanski, E. F.; Dorman, D. E.; Occolowitz, J. L.; Jones, N. D.; Chaney, M. O.; Hamill, R. L.; Hoehn, M. M. J. Antibiot. 1975, 28, 286.
9. (b) Bycroft, B.; Pinchin, R. J. C. S. Chem. Commun. 1975, 121.
10. 1b
11. 7. (a) Moazed, D.; Stern, S.; Noller, H. F. J. Mol. Biol. 1986, 187, 399.
12. (b) Moazed, D.; Noller, H. F. Nature 1987, 327, 389.
13. (c) Moazed, D.; Noller, H. F. Biochimie 1987, 69, 879.
14. (d) Stern, S.; Moazed, D.; Noller, H. F. Meths. in Enzymol. 1988, 164, 481.
15. 8. (a) Shiba, T.; Inami, K.; Sawada, K.; Hirotsu, Y. Heterocycles 1979, 13, 175.
16. (b) Inami, K.; Shiba, T. Tetrahedron Lett. 1984, 25, 2009.
17. (c) Inami, K.; Shiba, T. Bull. Chem. Soc. Jpn. 1985, 58, 352.
18. (d) Inami, K.; Shiba, T. Bull. Chem. Soc. Jpn. 1986, 59, 2185.
19. 9. Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1993, 775, 8449. (formula presented)
20. 8 (formula presented)
21. CH = 12.24 ppm.
22. 12. This reaction was found to proceed more cleanly in methanol than in ethanol, even though transesterification occurs with longer reaction times.