Total synthesis of bafilomycin A1. 1. Syntheses of the C5-C11, C12-C17 and C18-C25 segments

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 1069-1072

  Toshima, Kazunobu ^a   Jyojima, Takaaki ^a   Yamaguchi, Hiroyuki ^a   Murase, Hidekazu ^a   Yoshida, Taketo ^a   Matsumura, Shuichi ^a   Nakata, Masaya ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BAFILOMYCIN A1;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030045666     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02350-X     Document Type: Article

References (27)

1. (a) Werner, G.; Hagenmaier, H.; Albert, K.; Kohlshorn, H.; Drautz, H. Tetrahedron Lett. 1983, 24, 5193.
2. (b) Werner, G.; Hagenmaier, H.; Drautz, H.; Baumgartner, A.; Zähner, H. J. Antibiot. 1984, 37, 110.
3. Bowman, E. J.; Siebers, A.; Altendorf, K. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 7972.
4. Baker, G. H.; Brown, P. J.; Dorgan, R. J. J.; Everett, J. R.; Ley, S. V.; Slawin, A. M. Z.; William, D. J. Tetrahedron Lett. 1987, 28, 5565.
5. (a) Corey, E. J.; Ponder, J. W. Tetrahedron Lett. 1984, 25, 4325.
6. (b) Everett, J. R. J. Chem. Soc., Chem. Commun. 1987, 1878.
7. (a) Arcamone, F. M.; Bertazzoli, C.; Ghione, M.; Scotti, T. Gion. Microbiol. 1959, 7, 207.
8. (b) Arai, M. J. Antibiot. Ser. A. 1960, 13, 46 and 51.
9. (a) Kinashi, H.; Someno, K.; Sakaguchi, K.; Higashijima, T.; Miyazawa, T. Tetrahedron Lett. 1981, 22, 3857 and 3861.
10. (b) Kinashi, H.; Someno, K.; Sakaguchi, K. J. Antibiot. 1984, 37, 1333.
11. (a) Seto, H.; Akao, H.; Furihata, K.; Otake, N. Tetrahedron Lett. 1982, 23, 2667.
12. (b) Seto, H.; Tajima, I.; Akao, H.; Furihata, K.; Otake, N. J. Antibiot. 1984, 37, 610.
13. Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871.
14. (a) Roush, W. R.; Bannister, T. D. Tetrahedron Lett. 1992, 33, 3587.
15. (b) Roush, W. R.; Bannister, T. D.; Wendt, M. D. Tetrahedron Lett. 1993, 34, 8387.
16. Paterson, I.; Bower, S.; Mcleod, M. D. Tetrahedron Lett. 1995, 36, 175.
17. Toshima, K.; Yamaguchi, H.; Jyojima, T.; Noguchi, Y.; Nakata, M.; Matsumura, S. Tetrahedron Lett., following paper.
18. Mulzer, J.; Schulze, T.; Strecker, A.; Denzer, W. J. Org. Chem. 1988, 53, 4098.
19. Rand, C. L.; Van Horn, D. E.; Moore, M. W.; Negishi, E. J. Org. Chem. 1981, 46, 4096.
20. The DEIPS group in 2 was found to be a key protecting group for the total synthesis of 1. (a) Toshima, K.; Tatsuta, K.; Kinoshita, M. Tetrahedron Lett. 1986, 27, 4741.
21. (b) Toshima, K.; Mukaiyama, S.; Kinoshita, M.; Tatsuta, K. Tetrahedron Lett. 1989, 30, 6413.
22. Toshima, K.; Yanagawa, K.; Mukaiyama, S.; Tatsuta, K. Tetrahedron Lett. 1990, 31, 6697.
23. Kawabata, T.; Kimura, Y.; Ito, Y.; Terashima, S. Tetrahedron Lett. 1986, 27, 6241.
24. Takai, K.; Nitta, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5263.
25. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
26. Toshima, K.; Misawa, M.; Ohta, K.; Tatsuta, K.; Kinoshita, M. Tetrahedron Lett. 1989, 30, 6417.
27. 1H-NMR spectra [270MHz, CDCls, δ (TMS), J (Hz)] are the following. 2: 0.64 (4H, q, J = 7.7), 0.86 (3H, d, J = 7.0), 0.95-1.03 (16H, m), 1.21 (9H, s), 1.80 (3H, s), 1.8-1.93 (1H, m), 1.95-2.07 (1H, m), 2.02 (1H, dd, J = 13.0 and 10.8), 2.42 (1H, br dd, J = 13.0 and 3.0), 3.51 (1H, dd, J = 4.5 and 4.5), 3.87 (1H, dd, J = 11.0 and 7.3), 4.25 (1H, dd, J = 11.0 and 4.9), 5.85 (1H, br s). 3: 0.85-0.93 (15H, m), 1.10 (3H, d, J = 7.0), 1.24-1.38 (6H, m), 1.35 (3H, s), 1.37 (3H, s), 1.44-1.57 (6H, m), 1.77 (1H, m), 3.28 (3H, s), 3.40 (1H, ddd, J = 9.0, 6.3 and 1.2). 3.60 (1H, dd, J = 11.6 and 1.8), 3.82 (1H, dd, J = 9.0 and 2.2), 4.08 (1H, dd, J = 11.6 and 2.8), 5.79 (1H, dd, J = 19.0 and 6.3), 6.21 (1H, dd, J = 19.0 and 1.2). 4: 0.73 (3H, d, J = 7.0), 0.86 (3H, d, J = 6.9), 0.97 (9H, s), 0.99 (9H, s), 1.01 (3H, d, J = 7.0), 1.07 (3H, d, J = 7.1), 1.73 (1H, d septet, J = 7.0 and 2.1), 2.23 (1H, m), 2.38 (1H, dd, J = 14.2 and 3.4), 2.53 (1H, dq, J = 10.8 and 7.0), 2.56 (1H, dq, J = 10.8 and 7.0), 2.71 (1H, dd, J = 14.2 and 10.1), 3.68 (1H, dd, J = 9.6 and 2.1), 4.62 (1H, ddd, J = 10.1, 5.9 and 3.4).