Total Synthesis of a Monocyclic Peptide Lactone Antibiotic, Etamycin

Journal of the American Chemical Society

Volumn 95, Issue 3, 1973, Pages 875-879

  Sheehan, John C ^a   Ledis, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; CYCLOPEPTIDE; LACTONE;

ARTICLE; SYNTHESIS; TECHNIQUE;

ANTIBIOTICS; LACTONES; METHODS; PEPTIDES, CYCLIC;

EID: 0015916420     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00784a041     Document Type: Article

References (37)

1. H. Brockmann and H. Lackner, Naturwissenschaften, 47, 230 (1960).
2. H. Brockmann and H. Lackner, Naturwissenschaften, 51, 407 (1964).
3. H. Brockmann and H. Lackner, Naturwissenschaften, 51, 384, 435 (1964).
4. J. Meienhofer, Experientia, 24, 776 (1968).
5. M. A. Ondetti and P. L. Thomas, J. Amer. Chem. Soc., 87, 4373 (1965).
6. G. Jolles and J. Bouchaudon, Peptides, Proc. Eur. Symp., 8th, 1966, 258 (1967).
7. Yu. A. Ovchinnikov, A. A. Kiryushkin, and M. M. Shemyakin, Zh. Obshch. Khim., 36, 620 (1966).
8. Yu. A. Ovchinnikov, A. A. Kiryushkin, and M. M. Shemyakin, Chem. Abstr., 65, 9013d (1963).
9. M. M. Shemyakin, Yu. A. Ovchinnikov, A. A. Kiryushkin, and V. T. Ivanov, Izv. Akad. Nauk SSSR, Ser. Khim., 1623 (1965).
10. M. M. Shemyakin, Yu. A. Ovchinnikov, A. A. Kiryushkin, and V. T. Ivanov Chem. Abstr., 64, 2157g (1965).
11. Yu. A. Ovchinnikov, V. T. Ivanov, and I.I. Mikhaleva, Tetrahedron Lett., 159 (1971).
12. Yu. A. Ovchinnikov, V. T. Ivanov, P. V. Kostetskii, and M. M. Shemyakin, Khim. Prir. Soedin., 236 (1968).
13. Yu. A. Ovchinnikov, V. T. Ivanov, P. V. Kostetskii, and M. M. Shemyakin, Chem. Abstr., 70, 58261x (1968).
14. M. M. Shemyakin, N. A. Aldanova, E. I. Vinogradova, M. Yu. Feigina, Izv. Akad. Nauk SSSR, Ser. Khim., 2143 (1966).
15. M. M. Shemyakin, N. A. Aldanova, E. I. Vinogradova, M. Yu. Feigina, Chem. Abstr., 66, 85381z (1967).
16. M. M. Shemyakin, E. I. Vinogradova, M. Yu. Feigina, N. A. Aldanova, B. Shvetsov, and L. A. Ponina, Zh. Obshch. Khim., 36, 1391 (1966).
17. M. M. Shemyakin, E. I. Vinogradova, M. Yu. Feigina, N. A. Aldanova, B. Shvetsov, and L. A. Ponina, Chem. Abstr., 66, 11170k (1967).
18. J. C. Sheehan, H. G. Zachau, and W. B. Lawson, J. Amer. Chem. Soc., 80, 3349 (1958).
19. R. B. Arnold, A. W. Johnson, and A. B. Mauger, J. Chem. Soc., 4466 (1958).
20. B. Rozynov, Zh. Obshch. Khim., 139, 891 (1969).
21. H. Brockmann, et al, Angew. Chem., 68, 70 (1956).
22. H. Vanderhaeghe and G. Parmentier, J. Amer. Chem. Soc., 82, 4414 (1960).
23. F. W. Eastwood, R. K. Snell, and A. Todd, J. Chem. Soc., 2286 (1960).
24. A. A. Patchett and B. Witkop, J. Amer. Chem. Soc., 79, 185 (1957).
25. H. C. Beyerman and W. Massen van der Brink, Proc. Chem. Soc., London, 266 (1963).
26. E. Schroeder and K. Lubke, “The Peptides,” Vol. 1, Academic Press, New York, N. Y., 1965, p 144.
27. J. C. Sheehan and M. G. Howell, J. Org. Chem., 28, 2279 (1963).
28. H. Kotake, T. Saito, and K. Okubo, Bull. Chem. Soc. Jap., 42, 1367 (1969).
29. R. L. Cargill, Ph.D. Thesis, Massachusetts Institute of Technology, 1960.
30. P. Quitt, J. Hellerbach, and K. Vogler, Helv. Chim. Acta, 46, 327 (1963).
31. J. C. Sheehan, J. Preston, and P. A. Cruickshank, J. Amer. Chem. Soc., 87, 2492 (1965).
32. D. Heinert and A. E. Martell, Tetrahedron, 3, 49 (1958).
33. J. T. Sheehan, J. Org. Chem., 31, 636 (1966).
34. A. C. Cope, et al., J. Amer. Chem. Soc., 63, 3452 (1941).
35. C. S. Marvel and W. A. Noyes, J. Amer. Chem. Soc., 42, 2259 (1920).
36. M. Kune, G. Ovakimian, and P. A. Levene, J. Biol. Chem., 137, 337 (1941).
37. J. P. Greenstein and M. Winitz, “Chemistry of the Amino Acids,” Vol. 3, Wiley, New York, N. Y., 1961, pp 2022, 2038.