(+)-Trienomycins A, B, C, and F and (+)-mycotrienins I and II: Relative and absolute stereochemistry

Journal of the American Chemical Society

Volumn 118, Issue 35, 1996, Pages 8308-8315

  Smith III, Amos B ^a   Wood, John L ^a   Wong, Weichyun ^a   Gould, Alexandra E ^a   Rizzo, Carmelo J ^a   Barbosa, Joseph ^a   Komiyama, Kanki ^b   Omura, Satoshi ^b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANSAMYCIN DERIVATIVE; ANTIFUNGAL AGENT; MYCOTRIENIN I; MYCOTRIENIN II; TRIENOMYCIN A; TRIENOMYCIN B; TRIENOMYCIN C; TRIENOMYCIN F; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0029817345     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961400i     Document Type: Article

References (60)

1. (a) Funayama, S.; Okada, K.; Komiyama, K.; Umezawa, I. J. Antibiot. 1985, 38, 1107.
2. (b) Funayama, S.; Okada, K.; Iwasaki, K.; Komiyama, K.; Umezawa, I. J. Antibiot. 1985, 38, 1677.
3. (c) Nomoto, H.; Katsumata, S.; Takahashi, K.; Funayama, S.; Komiyama, K.; Umezawa, I.; Ōmura, S. J. Antibiot. 1989, 42, 479.
4. (a) Umezawa, I.; Funayama, S.; Okada, K.; Iwasaki, K.; Satoh, J.; Masuda, K.; Komiyama, K. J. Antibiot. 1985, 38, 699.
5. (b) Funayama, S.; Anraku, Y.; Mita, A.; Yang, Z.-B.; Shibata, K.; Komiyama, K.; Umezawa, I.; Ōmura, S. J. Antibiot. 1988, 41, 1223.
6. Hiramoto, S.; Sugita, M.; Andō, C.; Sasaki, T.; Furihata, K.; Seto, H.; Ōtake, N. J. Antibiot. 1985, 38, 1103.
7. (a) Sugita, M.; Natori, Y.; Sasaki, T.; Furihata, K.; Shimazu, A.; Seto, H.; Ōtake, N. J. Antibiot. 1982, 35, 1460.
8. (b) Sugita, M.; Sasaki, T.; Furihata, K.; Seto, H.; Ōtake, N. J. Antibiot. 1982, 35, 1467.
9. (c) Sugita, M.; Natori, Y.; Sueda, N.; Furihata, K.; Seto, H.; Ōtake, N. J. Antibiot. 1982, 35, 1474.
10. (d) Sugita, M.; Furihata, K.; Seto, H.; Ōtake, N.; Sasaki, T. Agric. Biol. Chem. 1982, 46, 1111.
11. (a) Damberg, M.; Russ, P.; Zeeck, A. Tetrahedron Lett. 1982, 23, 59.
12. (b) Lazar, G.; Zähner, H.; Damberg, M.; Zeeck, A. J. Antibiot. 1983, 36, 187.
13. (a) Wu, T. S.; Duncan, J.; Tsao, S. W.; Chang, C. J.; Keller, P. J.; Floss, H. G. J. Nat. Prod. 1987, 50, 108.
14. (b) Casati, R.; Beale, J. M.; Floss, H. G. J. Am. Chem. Soc. 1987, 109, 8102, and references cited therein.
15. Smith, A. B., III; Barbosa, J.; Wong, W.; Wood, J. L. J. Am. Chem. Soc. 1995, 117, 10777.
16. Smith, A. B., III; Wood, J. L.; Wong, W.; Gould, A. E.; Rizzo, C. J.; Funayama, S.; Ōmura, S. J. Am. Chem. Soc. 1990, 112, 7425.
17. Smith, A. B., III; Wood, J. L.; Ōmura, S. Tetrahedron Lett. 1991, 32, 841.
18. Smith, A. B., III; Wood, J. L.; Gould, A. E.; Ōmura, S.; Komiyama, K. Tetrahedron Lett. 1991, 32, 1627.
19. Doyle, M. P.; Van Oeveren, A.; Westrum, L. J.; Protopopova, M. N.; Clayton, T. W., Jr. J. Am. Chem. Soc. 1991, 113, 8982.
20. Preparation of hydroxy γ-lactone: (a) Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett. 1984, 1389. (b) Tanaka, A.; Yamashita, K. Synthesis 1987, 570. Conversion to O-methyl derivative: (c) Lardon, A.; Reichstein, T. Helv. Chim. Acta 1949, 32, 2003.
21. Preparation of hydroxy γ-lactone: (a) Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett. 1984, 1389. (b) Tanaka, A.; Yamashita, K. Synthesis 1987, 570. Conversion to O-methyl derivative: (c) Lardon, A.; Reichstein, T. Helv. Chim. Acta 1949, 32, 2003.
22. Preparation of hydroxy γ-lactone: (a) Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett. 1984, 1389. (b) Tanaka, A.; Yamashita, K. Synthesis 1987, 570. Conversion to O-methyl derivative: (c) Lardon, A.; Reichstein, T. Helv. Chim. Acta 1949, 32, 2003.
23. (a) Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989.
24. (b) Basha, A.; Lipton, M. F.; Weinreb, S. M. Tetrahedron Lett. 1977, 4171.
25. (c) Lipton, M. F.; Basha, A.; Weinreb, S. M. Org. Synth. 1979, 59, 49.
26. For a review of ozonolysis, see: Bailey, P. S. Ozonation in Organic Chemistry; Academic Press: New York, 1978; Vol. 1, Chapter 4, p 15.
27. Pihlaja, K.; Kellie, G. M.; Riddell, F. G. J. Chem. Soc., Perkin Trans. 2 1972, 252.
28. (a) MacroModel V2.5: Still, W. C.; Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Lipton, M.; Liskamp, R.; Chang, G.; Hendrickson, T.; DeGunst, F.; Hasel, W. Department of Chemistry, Columbia University, New York, NY 10027.
29. (b) Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 4379.
30. Coupling constants were determined in the NMR submode of MacroModel.
31. Wong, W. Ph.D. Thesis, University of Pennsylvania, Philadelphia, PA, 1993.
32. (a) Hanessian, S.; Murray, P. J. Tetrahedron 1987, 43, 5055.
33. (b) Hanessian, S.; Murray, P. J. J. Org. Chem. 1987, 52, 1170.
34. Trost, B. M.; Latimer, L. H. J. Org. Chem. 1978, 43, 1031.
35. See following article in this issue: Smith, A. B., III; Barbosa, J.; Wong, W.; Wood, J. L. J. Am. Chem. Soc. 1996, 118, 8316.
36. Fukuyama, T.; Nunes, J. J. J. Am. Chem. Soc. 1988, 110, 5196. Also see: Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2424.
37. Fukuyama, T.; Nunes, J. J. J. Am. Chem. Soc. 1988, 110, 5196. Also see: Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2424.
38. Following the CIP sequence rules, the analogous configuration of (+)-16 is designated 11S, 12S, 13R.
39. From ca. 100 mg of a mixture believed to contain only (+)-trienomycins B and C, we isolated ca. 3 mg of (+)-trienomycin F.
40. Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis; Springer-Verlag: New York, 1984; p 101.
41. The Weinreb aluminum amide couplings were accompanied by partial (ca. 10-22%) epimerization at C(28).
42. (a) See ref. 25, p 247.
43. (b) Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.
44. Chemical shift data are reported in ppm relative to internal TMS.
45. Nair, M. D.; Adams, R. J. Am. Chem. Soc. 1961, 83, 922.
46. Corey, E. J.; Gras, J.-L.; Ulrich, P. Tetrahedron Lett. 1976, 809.
47. Corey, E. J.; Cho, H.; Rücker, C.; Hua, D. H. Tetrahedron Lett. 1981, 22, 3455.
48. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
49. Acids 47 and 48 were prepared via coupling of D-alanine methyl ester with the symmetrical anhydrides of cyclohexanecarboxylic and tiglic acids, respectively, followed by ester hydrolysis.
50. BOC-D-alanine was purchased from Schweizerhall, Inc. (South Plainfield, NJ).
51. See ref 25, p 170.
52. (a) Castro, B.; Dormoy, J. R.; Evin, G.; Selve, C. Tetrahedron Lett. 1975, 1219.
53. (b) Castro, B.; Dormoy, J. R.; Dourtoglou, B.; Evin, G.; Selve, C.; Ziegler, J.-C. Synthesis 1976, 751.
54. (c) Castro, B.; Evin, G.; Selve, C.; Seyer, R. Synthesis 1977, 413.
55. A plausible pathway for the formation of (+)-50 under acidic conditions is illustrated below. The propensity of related model systems to form γ-lactams has also been observed in our laboratory (Wood, J. L., unpublished results).
56. Chang, C. D.; Waki, M.; Ahmad, M.; Meienhofer, J.; Lundell, E. O.; Haug, J. D. Int. J. Peptide Protein Res. 1980, 15, 59.
57. Zimmer, H.; Lankin, D. C.; Morgan, S. W. Chem. Rev. 1971, 71, 229.
58. We gratefully acknowledge a generous gift of (+)-mycotrienins I and II from Professor H. Seto (University of Tokyo).
59. Mycotrienin II has been converted to mycotrienols I and II: (a) ref 4c. (b) Sugita, M.; Hiramoto, S.; Andō, C.; Sasaki, T.; Furihata, K.; Seto, H.; Ōtake, N. J. Antibiot. 1985, 38, 799.
60. Mycotrienin II has been converted to mycotrienols I and II: (a) ref 4c. (b) Sugita, M.; Hiramoto, S.; Andō, C.; Sasaki, T.; Furihata, K.; Seto, H.; Ōtake, N. J. Antibiot. 1985, 38, 799.