Naturally occurring diazo compounds: The kinamycins

Current Organic Chemistry

Volumn 7, Issue 14, 2003, Pages 1433-1442

  Marco Contelles, José ^a   Molina, María T ^b  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZO COMPOUNDS; NATURALLY OCCURRING; SYNTHETIC STRATEGIES;

1 DEOXY 3 NORPREKINAMYCIN; 1,7 DIDEOXY 3 NORPREKINAMYCIN; BENZO[B]CARBAZOLOQUINONE CYANAMIDE DERIVATIVE; BENZO[B]FLUORENE DERIVATIVE; BENZ[F]INDENONE; CYSFLUORETIN; KINAFLUORENONE; KINAMYCIN; KINAMYCIN DERIVATIVE; KINOBSCURINONE; PHENATHROVIRIDIN AGLYCON; PREKINAMYCIN; PREKINAMYCIN DERIVATIVE; SEONGOMYCIN; STEALTHIN A; STEALTHIN B; STEALTHIN C; UNCLASSIFIED DRUG;

CYCLIZATION; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; EXPERIMENTATION; FRIEDEL CRAFTS REACTION; MEDICAL LITERATURE; NONHUMAN; REVIEW; STEREOCHEMISTRY; STREPTOMYCES MURAYAMAENSIS;

EID: 0043195579     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272033486396     Document Type: Review

References (71)

1. (a) Ito, S.; Matsuya, T.; Omura, S.; Otani, M.; Nakagawa, A.; Takeshima, H.; Iwai, Y.; Ohtani, M.; Hata, T. J. Antibiot. 1970, 23, 315-317 (kinamycins G and H not drawn in Chart 1, are peracetylated congeners with an isobutyroyl residue linked at O-C2 and at O-C1, respectively).
2. (a) Fusari, S. A.; Frohart, R. P.; Ryder, A.; Haskell, T. H.; Johannessen, D. W.; Elder, C. C.; Bartz, Q. R. J. Am. Chem. Soc. 1954, 76, 2878-2881;
3. (b) Dion, H. W.; Fusari, S. A.; Jahobowski, Z. L.; Zora, J. G.; Bartz, Q. R. J. Am. Chem. Soc. 1956, 78, 3075-3077;
4. (c) Imae, K.; Nihei, Y.; Oka, M.; Yamasaki, T.; Konishi, M. J. Antibiot. 1993, 46, 1031-1033.
5. (a) Carney, J. R.; Hong, A.-T.; Gould, S. J. Tetrahedron Lett. 1997, 38, 3119;
6. (b) Gould, S. J.; Melville, C. R. Bioorg. Med. Chem. Lett. 1995, 5, 51-54;
7. (c) Aoyama, T.; Zhao, W.; Kojima, F.; Muraoka, Y.; Naganawa, H.; Takeuchi, T.; Aoyagi, T. J. Antibiot. 1993, 46, 1471;
8. (d) Shin-Ya, K.; Furihata, K.; Teshima, Y.; Hayakawa, Y.; Seto, H. Tetrahedron Lett. 1992, 33, 7025.
9. (a) Hata, T.; Omura, S.; Iwai, Y.; Nakagawa, A.; Otani, M. J. Antibiot. 1971, 24, 353-359,
10. (b) Omura, S.; Nakagawa, A.; Yamada, H.; Hata, T.; Furusaki, A.; Watanabe, T. Chem. Pharm. Bull. 1971, 19, 2428-2430;
11. (c) Omura, S.; Nakagawa, A.; Yamada, H.; Hata, T.; Furusaki, A.; Watanabe, T. Chem. Pharm. Bull. 1973, 21, 931-940.
12. Arya, D. P.; Jebaratnam, D. J. J. Org. Chem. 1995, 60, 3268-3269.
13. (a) Gould, S. J. Chem. Rev. 1997, 97, 2499-2509;
14. (b) Knöller, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4262-4263.
15. Furusaki, A.; Matsui, M.; Watanabe, T.; Omura, S.; Nakagawa A.; Hata, T. Isr. J. Chem. 1972, 10, 173-187.
16. (a) Seaton, P. J.; Gould, S. J. J. Am. Chem. Soc. 1987, 109, 5282-5284;
17. (b) Cone, M. C.; Seaton, P. J.; Halley, K. A.; Gould, S. J. J. Antibiot. 1989, 42, 179-188;
18. (c) Seaton, P. J.; Gould, S. J. J. Antibiot. 1989, 42, 189-197.
19. Seaton, P. J.; Gould, S. J. J. Am. Chem. Soc. 1988, 110, 5912-5914.
20. Dmitrienko, G. I.; Nielsen, K. E.; Steingart, C.; Ming, N. S.; Willson, J. M.; Weeratunga, G. Tetrahedron Lett. 1990, 31, 3681-3684.
21. Echavarren, A. M.; Tamayo, N.; Paredes, M. C. Tetrahedron Lett. 1993, 34, 4713-4716.
22. Gould, S. J.; Tamayo, N.; Melville, C. R.; Cone, M. C. J. Am. Chem. Soc. 1994, 116, 2207-2208.
23. 13C NMR spectra for some structural assignments and some unusual rearrangements reported in Echavarren's paper-see reference 11-; soon after, Echavarren and co-wokers have corrected these values and explained the extent of these rearrangemente in the best experimental conditions (see reference 17)).
24. Hauser, F. M.; Zhou, M. J. Org. Chem. 1996, 61, 5722.
25. Gould, S. J.; Chem, J.; Cone, M. C.; Gore, M. P.; Melville, C. R.; Tamayo, N. J. Org. Chem. 1996, 61, 5720-5721.
26. Proteau, P. J.; Li, Y.; Chen, J.; Williamson, R. T.; Gould, S. J.; Laufer, R. S.; Dmitrienko, G. I. J. Am. Chem. Soc. 2000, 122, 8325-8326.
27. Echavarren, A. M.; Tamayo, N.; De Frutos, Ó.; García, A. Tetrahedron 1997, 53, 16835-16846.
28. (a) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138;
29. (b) Tamayo, N.; Echavarren, A. M.; Paredes, M. C. J. Org. Chem. 1991, 56, 6488.
30. Carter, A. H.; Race, E.; Rowe, F. H. J. Chem. Soc. 1942, 236.
31. Weeratunga, G.; Prasad, G. K. B.; Taylor, N. J.; Dmitrienko, G. I. Tetrahedron Lett. 1990, 31, 5713-5716.
32. Kobayashi, K.; Takeuchi, H.; Seko, S.; Suginome, H. Helv. Chim. Acta 1991, 74, 1091-1094.
33. (a) O'Sullivan, P. J.; Moreno, R. Murphy, W. S. Tetrahedron Lett. 1992, 33, 535-538.
34. (b) Shaw, K. J.; Luly, J. R.; Rapoport, H. J. Org. Chem. 1985, 50, 4515;
35. (c) Murayamia, K.; Osuka, A.; Nakagawa, K.; Nakeshima, T.; Tabuchi, K. Synthesis 1989, 628.
36. Cone, M. C.; Melville, C. R.; Gore, M. P.; Gould, S. J. J. Org. Chem. 1993, 58, 1058.
37. Gould, S. J.; Melville, C. R.; Cone, M. C.; Chen, J.; Carney, J. R. J. Org. Chem. 1997, 62, 320-324.
38. Carney, J. R.; Hong, S.-T.; Gould, S. J. Tetrahedron Lett. 1997, 38, 3139-3142.
39. Mohri, S.; Stefinovic, M.; Snieckus, V. J. Org. Chem. 1997, 62, 7072-7073.
40. (a) Gore, M. P.; Gould, S. J.; Weller, D. D. J. Org. Chem. 1991, 56, 2289-2291;
41. (b) Gore, M. P.; Gould, S. J.; Weller, D. D. J. Org. Chem. 1992, 57, 2774-2783.
42. For other approaches to phenathroviridin, see: (c) De Frutos, Ó.; Atienza, C.; Echavarren, A. M. Eur. J. Chem. 2001, 163-171 and reference 26.
43. (a) Li, T.; Wu, Y. L. J. Am. Chem. Soc. 1981, 103, 7009-7011;
44. (b) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178.
45. Oh-E, T.; Miyaura, N.; Suzuki, A. Synlett 1990, 221.
46. Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1988, 29, 2517.
47. (a) Qabaja, G.; Jones, G. B. Tetrahedron Lett. 2000, 41, 5317-5320;
48. (b) Qabaja, G.; Jones, G. B. J. Org. Chem. 2000, 65, 7187-7194.
49. (a) Mal, D.; Hazra, N. K.; Murty, K. V. S. N.; Majumdar, G. Synlett 1995, 1239-1240;
50. (b) Mal, D.; Ghorai, S.; Hazra, N. K. Indian J. Chem. 2001, 40B, 994-996;
51. (c) Mal, D.; Hazra, N. K. Tetrahedron Lett. 1996, 37, 2641-2642;
52. (d) Ghorai, S. K.; Roy, H. N.; Bandopadhyay, M.; Mal, D. J. Chem. Res. (S) 1999, 30-31.
53. Schmittel, M.; Keller, M.; Kiau, S.; Strittmatter, M. Chem. Eur. J. 1997, 3, 807.
54. De Frutos, Ó.; Echavarren, A. M. Tetrahedron Lett. 1997, 38, 7941-7942.
55. Rodríguez, D.; Castedo, L.; Domínguez, D.; Saá, C. Tetrahedron Lett. 1999, 40, 7701-7704.
56. Atienza, C.; Mateo, C.; De Frutos, Ó.; Echavarren, A. M. Org. Lett. 2001, 3, 153-155.
57. (a) Koyama, H.; Kamikawa, T. Tetrahedron Lett. 1997, 38, 3973-3976;
58. (b) Koyama, H.; Kamikawa, T. J. Chem. Soc., Perkin Trans. 1 1998, 203-209.
59. Williams, W.; Sun, X.; Jebaratnam, D. J. Org. Chem. 1997, 62, 4364-4369.
60. Duclos, R. I.; Tung, J. S.; Rapoport, H. J. Org. Chem. 1984, 49, 5243-5246.
61. Kometani, T.; Takeuchi, Y.; Yoshii, E. J. Chem. Soc. Perkin Trans. 1 1981, 1197-1202.
62. Tomioka, H.; Kawasaki, H.; Kobayashi, N.; Hirai, K. J. Am. Chem. Soc. 1995, 117, 4483-4498.
63. (a) Kumamoto, T.; Tabe, N.; Yamaguchi, K.; Ishikawa, T. Tetrahedron Lett. 2000, 41, 5693-5697;
64. (b) Kumamoto, T.; Tabe, N.; Yamaguchi, K.; Yagishita, H.; Iwasa, H.; Ishikawa, T. Tetrahedron 2001, 57, 2717-2728.
65. Kitani, Y.; Morita, A.; Kumamoto, T.; Ishikawa, T. Helv. Chim. Acta 2002, 85, 1186-1195.
66. Menger, F. M.; Chow, J. F.; Kaiserman, H.; Vasquez, P. C. J. Am. Chem. Soc. 1983, 105, 4996-5002.
67. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011-1013.
68. Danishefsky, S.; Yan, C.-F.; Singh, R. K.; Gammil, R. B.; McMurray, Jr., P. M.; Fritsch, N.; Clardy, J. J. Am. Chem. Soc. 1979, 101, 7001-7008.
69. Hannan, R. L.; Barber, R. B.; Rapoport, H. J. Org. Chem. 1979, 44, 2153.
70. Jones, G. Org. React. 1967, 15, 204-599.
71. Nicolaou, K. C. N.; Zhong, Y.-L.; Baran, P. S. J. Am. Chem. Soc. 2000, 122, 7596.