Total synthesis of a macrocyclic antibiotic, micrococcin P

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 7, 1999, Pages 1561-1569

  Okumura, Kazuo ^a   Nakamura, Yutaka ^a   Shin, Chung Gi ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; MICROCCIN P; UNCLASSIFIED DRUG;

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

EID: 0032764171     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.1561     Document Type: Article

References (26)

1. a) P. Brookes, A. T. Fuller, and J. Walker, J. Chem. Soc., 1957, 689.
2. b) J. Walker, A. Olesker, L. Valente, R. Rabanal, and G. Lukacs, J. Chem. Soc., Chem. Commun., 1977, 706.
3. c) B. W. Bycroft and M. S. Gowland, J. Chem. Soc., Chem. Commun., 1978, 256.
4. For examples: M. Debono, R. M. Molly, J. L. Occlowitz, J. W. Paschel, A. H. Hunt, K. H. Michel, and J. W. Martin, J. Org. Chem., 57, 5200 (1992); H. Abe, K. Kushida, Y. Shiobara, and M. Kodama, Tetrahedron Lett., 29, 1401 (1998).
5. For examples: M. Debono, R. M. Molly, J. L. Occlowitz, J. W. Paschel, A. H. Hunt, K. H. Michel, and J. W. Martin, J. Org. Chem., 57, 5200 (1992); H. Abe, K. Kushida, Y. Shiobara, and M. Kodama, Tetrahedron Lett., 29, 1401 (1998).
6. C. Shin, K. Okumura, M. Shigekuni, and Y. Nakamura, Chem. Lett., 1998, 139.
7. K. Okumura, A. Ito, D. Yoshioka, and C. Shin, Heterocycles, 48, 1319 (1998).
8. K. Okumura, M. Shigekuni, Y. Nakamura, and C. Shin, Chem. Lett., 1996, 1025.
9. J. P. Sanches, T. F. Mich, and G. G. Huang, J. Heterocycl. Chem., 31, 297 (1994).
10. K. Okumura, H. Saito, C. Shin, K. Umemura, and J. Yoshimura, Bull. Chem. Soc. Jpn., 71, 1863 (1998).
11. a) E. Seva, G. Beretta, N. Montanini, G. S. Saddler, L. Gastaldo, P. Ferrari, R. Lorenzetti, P. Landini, F. Ripamonti, B. P. Goldstein, M. Berti, L. Montanaro, and M. Denaro, J. Antibiot., 44, 693 (1991).
12. b) J. Kettenring, L. Colombo, P. Ferrari, P. Tavecchia, M. Nebuloni, K. Vekey, G. G. Gallo, and E. Selva, J. Antibiot., 44, 702 (1991).
13. J. Shoji, T. Kato, Y. Yoshimura, and K. Tiri, J. Antibiot., 34, 1126 (1981).
14. S. Stella, N. Montanini, F. L. Monnier, P. Ferrari, L. Colombo, P. Landini, I. Ciciliato, B. P. Goldstein, E. Selva, and M. Denaro, J. Antibiot., 48, 780 (1995).
15. S. A. Rhone-Poulenc, U. S. Patent 3155581 (1962), Fr. Patent 1392453 (1961); H. Depire, J. Thomas, and A. Brun, Tetrahedron Lett., 1977, 1397 and 1401; T. Prange, A. Ducruix, and C. Pascard, Nature, 265, 6418 (1977); C. Pascard, A. Ducruix, J. Lunel, and T. Prange, J. Am. Chem. Soc., 99, 6418 (1977).
16. S. A. Rhone-Poulenc, U. S. Patent 3155581 (1962), Fr. Patent 1392453 (1961); H. Depire, J. Thomas, and A. Brun, Tetrahedron Lett., 1977, 1397 and 1401; T. Prange, A. Ducruix, and C. Pascard, Nature, 265, 6418 (1977); C. Pascard, A. Ducruix, J. Lunel, and T. Prange, J. Am. Chem. Soc., 99, 6418 (1977).
17. S. A. Rhone-Poulenc, U. S. Patent 3155581 (1962), Fr. Patent 1392453 (1961); H. Depire, J. Thomas, and A. Brun, Tetrahedron Lett., 1977, 1397 and 1401; T. Prange, A. Ducruix, and C. Pascard, Nature, 265, 6418 (1977); C. Pascard, A. Ducruix, J. Lunel, and T. Prange, J. Am. Chem. Soc., 99, 6418 (1977).
18. S. A. Rhone-Poulenc, U. S. Patent 3155581 (1962), Fr. Patent 1392453 (1961); H. Depire, J. Thomas, and A. Brun, Tetrahedron Lett., 1977, 1397 and 1401; T. Prange, A. Ducruix, and C. Pascard, Nature, 265, 6418 (1977); C. Pascard, A. Ducruix, J. Lunel, and T. Prange, J. Am. Chem. Soc., 99, 6418 (1977).
19. Y. Nakamura, C. Shin, K. Umemura, and J. Yoshimura, Chem. Lett., 1992, 1025.
20. C. Shin, Y. Nakamura, Y. Yamada, Y. Yonezawa, K. Umemura, and J. Yoshimura, Bull. Chem. Soc. Jpn., 68, 3151 (1995).
21. Y. Yamada, M. Shibata, T. Sugiura, S. Kato, and T. Shioiri, J. Org. Chem., 52, 1252 (1987).
22. U. Schmidt, P. Gleich, H. Griesser, and R. Utz, Synthesis, 1986, 992.
23. R. B. Woodward, K. Heusler, J. Gosteli, P. Naegeli, W. Oppolzer, R. Ramage, R. Ramganthan, and H. Vorbruggen, J. Am. Chem. Soc., 88, 825 (1966).
24. a) R. C. Kelly, I. Ebhard, and N. Wicnienski, J. Org. Chem., 51, 4590 (1986).
25. b) M. W. Bredenkamp, C. W. Holzapfel, and W. Van Zyl, Synth. Commun., 20, 2235 (1990).
26. BOP = (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate.