Total synthesis of streptonigrone

Journal of Organic Chemistry

Volumn 72, Issue 22, 2007, Pages 8489-8495

  Chan, Bryan K ^a   Ciufolini, Marco A ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONALIZATION; PYRIDONES; STREPTONIGRONE;

NEGATIVE IONS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

PYRIDONE DERIVATIVE; QUINOLINE; STREPTONIGRONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

MOLECULAR STRUCTURE; STEREOISOMERISM; STREPTONIGRIN;

EID: 35548941454     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701435p     Document Type: Article

References (69)

1. Isolation: (a) Herlt, A. J.; Rickards, R. W.; Wu, J. P. J. Antibiot. 1985, 38, 516.
2. (b) Kozlova, N. V.; L'vova, N. A.; Lapchinskaya, O. A.; Dokuchaeva, E. B.; Rubasheva, L. M.; Rozynov, B. V.; Preobrazhenskaya, M. N. Antibiot. Khim. 1990, 35, 13.
3. Preparation by oxidative decarboxylation of streptonigrin: (c) Preobrazhenskaya, M. N.; Holpne-Kozlova, N. V.; Lazhko, E. I. J. Antibiot. 1991, 45, 227.
4. Imino derivative and bioactivity thereof: (d) Tolstikov, V. V.; Preobrazhenskaya, M. N.; Balzarini, J.; De Clercq, E. J. Antibiot. 1992, 45, 1002.
5. Reviews: (a) Gould, S. J.; Weinreb, S. M. Prog. Chem. Org. Nat. Prod. 1982, 41, 77.
6. (b) Bringmann, G.; Reichert, Y.; Kane, V. V. Tetrahedron 2004, 60, 3539.
7. Structural work: (c) Tennant, S.; Rickards, R. W. Tetrahedron 1997, 53, 15101.
8. Severina, I. S.; Pyatakova, N. V.; Postnikov, A. B.; Preobrazhenskaya, M. N.; Khropov, Y. V. Eur. J. Pharmacol. 2004, 483, 127.
9. Liu, W. C.; Barbacid, M.; Bulgar, M.; Clark, J. M.; Crosswell, A. R.; Dean, L.; Doyle, T. W.; Fernandes, P. B.; Huang, S.; Manne, V.; Pirnik, D. M.; Wells, J. S.; Meyers, E. J. Antibiot. 1992, 45, 454.
10. Yamashita, Y.; Kawada, S.; Fujii, N.; Nakano, H. Cancer Res. 1990, 50, 5841.
11. Okada, H.; Mukai, H.; Inouye, Y.; Nakamura, S. J. Antibiot. 1986, 39, 306.
12. For a recent contribution see: Fryatt, T.; Pettersson, H. I.; Gardipee, W. T.; Green, S. J.; Slawin, A. M. Z.; Beall, H. D.; Moody, C. J. Bioorg. Med. Chem. 2004, 12, 1667, and references cited therein.
13. Streptonigrin: (a) Weinreb, S. M. Strategies Tactics Org. Synth. 1984, 1, 325.
14. (b) Weinreb, S. M.; Basha, F. Z.; Hibino, S.; Khatri, N. A.; Kim, D.; Pye, W. E.; Wu, T.-T. J. Am. Chem. Soc. 1982, 104, 536.
15. (c) Basha, F. Z.; Hibino, S.; Kim, D.; Pye, W. E.; Wu, T.-T.; Weinreb, S. M. J. Am. Chem. Soc. 1980, 102, 3962.
16. Streptonigrin: (a) Kende, A. S.; Lorah, D. P.; Boatman, R. J. J. Am. Chem. Soc. 1981, 103, 1271.
17. (b) Kende, A. S.; Ebetino, F. H.; Battista, R.; Boatman, R. J.; Lorah, D. P.; Lodge, E. Heterocycles 1981, 21, 91.
18. Lavendamycin: (c) Kende, A. S.; Ebetino, F. H. Tetrahedron Lett. 1984, 25, 923.
19. Reviews: (a) Boger, D. L. Chem. Rev. 1986, 86, 781.
20. (b) Boger, D. L. Strategies Tactics Org. Synth. 1988, 2, 1.
21. Streptonigrin: (c) Boger, D. L.; Panek, J. S. J. Am. Chem. Soc. 1985, 107, 5745.
22. (d) Boger, D. L.; Panek, J. S. J. Org. Chem. 1983, 48, 621.
23. Lavendamycin: (e) Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem. 1985, 50, 5790.
24. (f) Medicinal, chemistry studies: Boger, D. L.; Yasuda, M.; Mitscher, L. A.; Drake, S. D.; Kitos, P. A.; Thompson, S. C. J. Med. Chem. 1987, 30, 1918.
25. See ref 2, as well as: (a) Kametani, T.; Kozuka, A.; Terui, T. Yakugaku Zasshi 1973, 93, 406.
26. (b) Hibino, S.; Okazaki, M.; Ichikawa, M.; Sato, K.; Ishizu, T. Heterocycles 1985, 23, 261.
27. (c) Rama Rao, A. V.; Chavan, S. P.; Sivadasan, L. Tetrahedron 1986, 42, 5065.
28. (d) Rama Rao, A. V. Recent Prog. Chem. Synth. Antibiot. 1990, 497.
29. (e) Godard, A.; Rocca, P.; Fourquez, J.-M.; Rovera, J.-C.; Marsais, F.; Queguiner, G. Tetrahedron Lett. 1993, 34, 7919.
30. (f) Molina, P.; Murcia, F.; Fresneda, P. M. Tetrahedron Lett. 1994, 35, 1453.
31. (g) Godard, A.; Marsais, F.; Ple, N.; Trecourt, F.; Turck, A.; Queguiner, G. Heterocycles 1995, 40, 1055.
32. (h) Behforouz, M.; Haddad, J.; Cai, W.; Arnold, M. B.; Mohammadi, F.; Sousa, A. C.; Horn, M. A. J. Org. Chem. 1996, 61, 6552.
33. (i) Robinson, J. M.; Ahmed, M.; Alaniz, N. J.; Boyles, T. P.; Brasher, C. D.; Floyd, K. A.; Holland, P. L.; Maruffo, L. D.; McMahan, T. L.; Middleton, S.; O'Hara, K. D.; Pack, M. J.; Reynolds, B. D.; Rodriquez, R. R.; Sawyer, D. E.; Sharp, E.; Simpson, S. L.; Vanlandingham, C. L.; Velasquez, R. S.; Welch, B. M.; Wright, C. D. J. Hetercycl. Chem. 1998, 35, 65.
34. (j) Holzapfel, C. W.; Marais, W. J. Chem. Res., Synop. 2002, 22.
35. (k) McElroy, W. T.; DeShong, P. Org. Lett. 2003, 5, 4779.
36. (a) Ciufolini, M. A.; Byrne, N. E. J. Chem. Soc., Chem. Commun. 1988, 1230.
37. (b) Ciufolini, M. A.; Bishop, M. J. J. Chem. Soc., Chem. Commun. 1993, 1463.
38. (c) Ciufolini, M. A. Adv. Heterocycl. Nat. Prod. Synth. 1996, 3, 1.
39. Jain, R.; Roschangar, F.; Ciufolini, M. A. Tetrahedron Lett. 1995, 36, 3307.
40. Carles, L.; Narkunan, K.; Penlou, S.; Rousset, L.; Bouchu, D.; Ciufolini, M. A. J. Org. Chem. 2002, 66, 4304.
41. (a) Ciufolini, M. A.; Roschangar, F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1692.
42. (b) Ciufolini, M. A.; Roschangar, F. Tetrahedron 1997, 53, 11049.
43. (c) Ciufolini, M. A.; Roschangar, F. Targets Heterocycl. Syst. 2000, 4, 25.
44. (a) Boger, D. L.; Cassidy, K. C.; Nakahara, S. J. Am. Chem. Soc. 1993, 115, 10733.
45. (b) Boger, D. L.; Nakahara, S. J. Org. Chem. 1991, 56, 880.
46. See also (c) Boger, D. L. Chemtracts: Org. Chem. 1996, 9, 149.
47. (a) Kametani, T.; Kozuka, A.; Tanaka, S. Yakugaku Zasshi 1970, 90, 1574.
48. (b) Kametani, T.; Kano, S.; Watanabe, Y. Yakugaku Zasshi 1966, 86, 417.
49. Downer, N. K.; Jackson, A. J. Org. Biomol. Chem. 2004, 2, 3039.
50. (a) Heindel, N. D.; Bechara, I. S.; Kennewell, P. D.; Molnar, J.; Ohnmacht, C. J.; Lemke, S. M.; Lemke, T. F. J. Med. Chem. 1968, 11, 1218.
51. (b) Kaslow, C. E.; Nix, S. J. J. Org. Chem. 1951, 16, 895.
52. 3N, a minor degree of overreduction of 12 to 17 occurs only after an extended (> 12 h) contact time.
53. Experimental procedures and characterization data for compounds not directly related to 1 are provided as Supporting Information.
54. 2.
55. 13C lines at ca. 104, 118, and 142 ppm. Hardcopy spectra are provided as Supporting Information.
56. Substituent Z was H in chalcones 25 related to camptothecin. Such enones cyclized to indolizines only upon exposure to Lewis acidic agents, in contrast to the more electrophilic, "doubly activated" enones (Z = COOEt, etc.), which cyclize spontaneously.
57. Calculations carried out with the Hyperchem package.
58. Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org Chem. 1993, 58, 611.
59. Leblanc, Y.; Boudreault. J. Org. Chem. 1995, 60, 4268.
60. 2.
61. (a) Tamura, Y.; Fujita, M.; Chen, L. C.; Kiyokawa, H.; Ueno, K.; Kita, Y. Heterocycles 1981, 15, 871.
62. (b) Schoenen, B.; Zymalkowski, F. Archiv. Pharm. 1981, 314, 464.
63. 3 or with MsNHNa proceeded poorly.
64. (a) Shiori, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203.
65. (b) Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151.
66. (a) Jung, M. E.; Lyster, M. A. J. Org Chem. 1977, 42, 3761.
67. (b) Peters, R.; Althaus, M.; Diolez, C.; Rolland, A.; Manginot, E.; Veyrat, M. J. Org. Chem. 2006, 71, 7583.
68. 13C NMR chemical shifts for synthetic and natural 1 is provided as Supporting Information.
69. Experimental protocols are provided as Supporting Information.