Iromycins: A new family of pyridone metabolites from Streptomyces sp. II. Convergent total synthesis

Journal of Organic Chemistry

Volumn 72, Issue 14, 2007, Pages 5091-5097

  Shojaei, Heydar ^a   Li Böhmer, Zhen ^a   Von Zezschwitz, Paultheo ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATION; IROMYCINS; LIQUID AMMONIA; PYRIDONE;

AMMONIA; BACTERIA; ENZYME INHIBITION; ESTERS; METABOLITES; TRANSITION METALS;

ANTIBIOTICS;

6 BROMOMETHYLPYRONE; ALKYNE DERIVATIVE; COPPER; IROMYCIN; IROMYCIN A; NICKEL; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE INHIBITOR; PALLADIUM; PYRIDONE DERIVATIVE; PYRONE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; BROMINATION; CATALYST; CHEMICAL STRESS; ENZYME INHIBITION; REACTION ANALYSIS; STREPTOMYCES; SYNTHESIS;

ALKENES; CATALYSIS; METALS; METHYLATION; MOLECULAR STRUCTURE; PYRIDONES; STREPTOMYCES;

EID: 34447295369     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070327j     Document Type: Article

References (62)

1. (a) Surup, F.; Wagner, O.; von Frieling, J.; Schleicher, M.; Oess, S.; Muller, P.; Grond, S. J. Org. Chem. 2007, 72, 5085-5090.
2. (b) Sukenaga, Y.; Yamazaki, T.; Aoyama, T.; Takayasu, Y.; Harada, T. Japan Patent JP10 237044, 1998; Chem. Abstr. 1998, 129, 244203S.
3. (a) Williams, D. R.; Sit, S.-Y. J. Org. Chem. 1982, 47, 2846-2851.
4. (b) Williams, D. R.; Bremmer, M. L.; Brown, D. L.; D'Antuono, J. J. Org. Chem. 1985, 50, 2807-2809.
5. (c) Irlapati, N. R.; Adlington, R. M.; Conte, A.; Pritchard, G. J.; Marquez, R.; Baldwin, J. E. Tetrahedron 2004, 60, 9307-9317.
6. (d) Hogg, T.; Mesters, J. R.; Hilgenfeld, R. Curr. Protein Pept. Sci. 2002, 3, 121-131.
7. (a) Graber, M. A.; Gerwick, W. H. J. Nat. Prod. 1998, 61, 677-680.
8. (b) Yano, K.; Yokoi, K.; Sato, J.; Oono, J.; Kouda, T.; Ogawa, Y.; Nakashima, T. J. Antibiot. 1986, 39, 38-43.
9. (c) Takahashi, N.; Suzuki, A.; Tamura, S. J. Am. Chem. Soc. 1965, 87, 2066-2068.
10. (a) Schnermann, M. J.; Romero, F. A.; Hwang, I.; Nakamaru-Ogiso, E.; Yagi, T.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 11799-11807.
11. (b) Keaton, K. A.; Phillips, A. J. J. Am. Chem. Soc. 2006, 128, 408-409.
12. (c) Ono, M.; Yoshida, N.; Akita, H. Chem. Pharm. Bull. 1997, 45, 1745-1750.
13. (d) Schmidtchen, F. P.; Rapoport, H. J. Am. Chem. Soc. 1977, 99, 7014-7019.
14. Shimamura, H.; Sunazuka, T.; Izuhara, T.; Hirose, T.; Shiomi, K.; Omura, S. Org. Lett. 2007, 9, 65-67.
15. Hart, D. W.; Blackburn, T. F.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 679-680.
16. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769-3772.
17. (a) Negishi, E.-i; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639-6647.
18. (b) Lipshutz, B. H.; Bulow, G.; Fernandez-Lazaro, F.; Kim, S.-K.; Lowe, R.; Mollard, P.; Stevens, K. L. J. Am. Chem. Soc. 1999, 121, 11664-11673.
19. Harris, T. M.; Harris, C. M. Tetrahedron 1969, 25, 2687-2691.
20. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082-1087.
21. (a) Spencer, R. W.; Copp, L. J.; Pfister, J. R. J. Med. Chem. 1985, 28, 1828-1832.
22. (b) Kanazawa, T.; Ohkawa, Y.; Kuda, T.; Minobe, Y.; Tani, T.; Nishizawa, M. Chem. Pharm. Bull. 1997, 45, 1046-1051.
23. (c) Oster, T. A.; Harris, T. M. Tetrahedron Lett. 1983, 24, 1851-1854.
24. (d) Wolberg, M.; Ji, A.; Hummel, W.; Müller, M. Synthesis 2001, 937-942.
25. (e) Shone, R. L.; Deason, J. R.; Miyano, M. J. Org. Chem. 1986, 51, 268-270.
26. (f) Ishibashi, Y.; Ohba, S.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 2997-3000.
27. The acidity of such 4-hydroxypyran-2-ones is comparable to that of acetic acid: Ferri, D.; Bürgi, T.; Baiker, A. J. Chem. Soc Perkin Trans. 2 2002, 437-441.
28. Köster, G.; Hoffmann, R. W. Liebigs Ann. Chem. 1987, 987-990 and references therein.
29. Pyrone 14 could also be acetylated in 69% yield (see Supporting Information), yet this protecting group turned out to be unstable in the subsequent transformations.
30. (a) Groutas, W. C.; Stanga, M. A.; Brubaker, M. J.; Huang, T. L.; Moi, M. K.; Carroll, R. C. J. Med. Chem. 1985, 28, 1106-1109.
31. (b) El-Kholy, I. E.; Mishrikey, M. M.; Abdoul-Ela, S. L. J. Heterocycl. Chem. 1982, 19, 1329-1334.
32. (a) Bloomer, J. L.; Zaidi, S. M. H.; Strupczewski, J. T.; Brosz, C. S.; Gudzyk, L. A. J. Org. Chem. 1974, 39, 3615-3616.
33. (b) Bacardit, R.; Moreno-Manas, M.; Pleixats, R. J. Heterocycl. Chem. 1982, 19, 157-160.
34. Jeromin, G. E.; Orth, W.; Rapp, B.; Weiss, W. Chem. Ber. 1987, 120, 649-651.
35. (a) Kaga, H.; Goto, K.; Takahashi, T.; Hino, M.; Tokuhashi, T.; Orito, K. Tetrahedron 1996, 52, 8451-8470.
36. (b) Jacoby, D.; Célérier, J. P.; Petit, H.; Lhommet, G. Synthesis 1990, 301-304.
37. Zweifel, G.; Miller, J. A. Org. React. 1984, 32, 375-517 and references therein.
38. Wipf, P.; Lim, S. Angew. Chem. 1993, 105, 1095-1097;
39. Angew. Chem. Int. Ed. Engl. 1993, 32, 1068-1071.
40. (a) Negishi, E.-i; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel B. I. J. Am. Chem. Soc. 1978, 100, 2254-2256.
41. (b) Negishi, E.-i; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393-2401.
42. (c) Matsushita, H.; Negishi, E.-i. J. Am. Chem. Soc. 1981, 103, 2882-2884.
43. (d) Negishi, E.-i.; Chatterjee, S.; Matsushita, H. Tetrahedron Lett. 1981, 22, 3737-3740.
44. (e) Negishi, E.-i.; Matsushita, H.; Okukado, N. Tetrahedron Lett. 1981, 22, 2715-2718.
45. (f) Negishi, E.-i.; Baba, S. J. Chem. Soc., Chem. Commun. 1976, 596-597.
46. (a) Lipshutz, B. H.; Bülow, G.; Lowe, R. F.; Stevens, K. L. Tetrahedron 1996, 52, 7265-7276.
47. (b) Lipshutz, B. H.; Kim, S.-K.; Mollard, P.; Blomgren, P. A.; Stevens, K. L. Tetrahedron 1998, 54, 6999-7012.
48. (a) Lipshutz, B. H.; Kim, S.-K.; Mollard, P.; Stevens, K. L. Tetrahedron 1998, 54, 1241-1253.
49. (b) Tatsuta, K.; Tamura, T. J. Antibiot. 2000, 53, 418-421.
50. (c) Negishi, E.-i.; Liou, S.-Y.; Xu, C.; Huo, S. Org. Lett. 2002, 4, 261-264.
51. 3 was employed.
52. For a study on the oxidative addition of benzyl halides to Ni(0) complexes leading to formation of dibenzyl, see: Bartsch, E.; Dinjus, E.; Fischer, R.; Uhlig, E. Z. Anorg. Allg. Chem. 1977, 433, 5-12.
53. For other examples of protiodepalladations, see: Voigt, K.; von Zezschwitz, P.; Rosauer, K.; Lansky, A.; Adams, A.; Reiser, O.; de Meijere, A. Eur. J. Org. Chem. 1998, 1521-1534.
54. (a) Lynd, R. A.; Zweifel, G. Synthesis 1974, 658-659.
55. (b) Flemming, S.; Kabbara, J.; Nickisch, K.; Westermann, J.; Mohr, J. Synlett 1995, 183-185.
56. (c) Zweifel, G.; Miller, R. L. J. Am. Chem. Soc. 1970, 92, 6678-6679.
57. Wipf, P.; Smitrovich, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178-3186.
58. For an example of a copper-catalyzed 1,4-addition to an enone in which a slight variation of the substrate completely inverted this selectivity, see: Lipshutz, B. H.; Dimock, S. H. J. Org. Chem. 1991, 56, 5761-5763.
59. (a) Eisch, J. J.; Damasevitz, G. A. J. Org. Chem. 1976, 41, 2214-2215.
60. (b) Uchida, K.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1976, 41, 2215-2217.
61. (c) Baba, S.; Van Horn, D. E.; Negishi, E.-i. Tetrahedron Lett. 1976, 17, 1927-1930.
62. All these compounds slowly start to decompose even when stored either neat or in solution at -18°C.