Chiral aziridinyl radicals: An application to the synthesis of the core nucleus of FR-900482

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 1083-1094

  Ziegler, Frederick E ^a   Belema, Makonen ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 FORMYL 6,9 DIHYDROXY 14 OXA 1,11 DIAZATETRACYCLO[7.4.1.0 2,7 0 10,12]TETRADECA 2,4,6 TRIEN 8 YLMETHYLCARBAMATE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031002685     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961992n     Document Type: Article

References (75)

1. Shimomura, K.; Hirai, O.; Mizota, T.; Matsumoto, S.; Mori, J.; Shibayama, F.; Kikuchi, H. J. Antibiot. 1987, 40, 600.
2. Hirai, O.; Shimomura, K.; Mizota, T.; Matsumoto, S.; Mori, J.; Kikuchi, H. J. Antibiot. 1987, 40, 607.
3. Iwami, M.; Kiyoto, S.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1987, 40, 589.
4. Kiyoto, S.; Shibata, T.; Yamashita, M.; Komori, T.; Okuhara, M.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1987, 40, 594.
5. Uchida, I.; Takase, S.; Kayakiri, H.; Kiyoto, S.; Hashimoto, M.; Tada, T.; Koda, S.; Morimoto, Y. J. Am. Chem. Soc. 1987, 109, 4108.
6. Fujita, T.; Takase, S.; Otsuka, T.; Terano, H.; Kohsaka, M. J. Antibiot. 1988, 41, 392.
7. Terano, H.; Takese, S.; Hosoda, J.; Kohsaka, M. J. Antibiot. 1989, 42, 145.
8. Shimomura, K.; Manda, T.; Mukumoto, S.; Masuda, K.; Nakamura, T.; Mizota, T.; Matsumoto, S.; Nishigaki, F.; Oku, T.; Mori, J.; Shibayama, F. Cancer Res. 1988, 48, 1166.
9. Masuda, K.; Nakamura, T.; Mizota, T.; Mori, J.; Shimomura, K. Cancer Res. 1988, 48, 5172.
10. Masuda, K.; Nakamura, T.; Shimomura, K.; Shibata, T.; Terano, H.; Kohsaka, M. J. Antibiot. 1988, 41, 1497.
11. Woo, J.; Sigurdsson, S. T.; Hopkins, P. B. J. Am. Chem. Soc. 1993, 115, 1199.
12. Williams, R. M.; Rajski, S. R. Tetrahedron Lett. 1993, 34, 7023.
13. Huang, H.; Pratum, T. K.; Hopkins, P. B. J. Am. Chem. Soc. 1994, 116, 2703.
14. Huang, H.; Rajski, S. R.; Williams, R. M.; Hopkins, P. B. Tetrahedron Lett. 1994, 35, 9669.
15. Yasuda, N.; Williams, R. M. Tetrahedron Lett. 1989, 30, 3397.
16. Jones, R. J.; Rapoport, H. J. Org. Chem. 1990, 55, 1144.
17. McClure, K. F.; Benbow, J. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1991, 113, 8185.
18. McClure, K. F.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 850.
19. Dmitrienko, G. I.; Denhart, D.; Mithani, S.; Prasad, G. K. B.; Taylor, N. J. Tetrahedron Lett. 1992, 33, 5705.
20. McClure, K. F.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 6094.
21. Martin, S. F.; Wagman, A. S. Tetrahedron Lett. 1995, 36, 1169.
22. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108.
23. Lim, H.-J.; Sulikowski, G. A. Tetrahedron Lett. 1996, 37, 5243.
24. Fukuyama, T.; Xu, L.; Goto, S. J. Am. Chem. Soc. 1992, 114, 383.
25. Schkeryantz, J. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 4722.
26. Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3471.
27. Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475.
28. Katoh, T.; Yoshino, T.; Nagata, Y.; Nakatani, S.; Terashima, S. Tetrahedron Lett. 1996, 37, 3479.
29. Ziegler, F. E.; Belema, M. J. Org. Chem. 1994, 59, 7962.
30. Ziegler, F. E.; Harran, P. G. J. Org. Chem. 1993, 58, 2768.
31. Ziegler, F. E.; Harran, P. G. Tetrahedron Lett. 1993, 34, 4505.
32. Nielson, O. B. T.; Bruun, H.; Bretting, C.; Feit, P. W. J. Med. Chem. 1975, 18, 41.
33. The molar ratio of ammonium sulfide to 3,5-dinitro-p-toluic acid was increased from 1:1 to 3:1. Barben, I. K.; Suschitzky, H. J. Chem. Soc. 1960, 672.
34. Batcho, A. D.; Leimgruber, W. Organic Syntheses; John Wiley: New York, 1985; Vol. 63, p 214.
35. James, P. N.; Snyder, H. R. Organic Syntheses; John Wiley: New York, 1963; Coll. Vol. IV, p 539.
36. Dunigan, J.; Weigel, L. J. Org. Chem. 1991, 56, 6225.
37. Barton, D. H. R.; Samadi, M. Tetrahedron 1992, 48, 7083.
38. We thank Mr. Mikhail Berlin of this laboratory for this observation.
39. The yield of alcohol 22b is the average obtained by combining the products of several runs.
40. Mitomycin numbering is used throughout the text for mitomycin-like structures. FR-900482 numbering is employed for related oxygen-bridged structures. These numbers may not agree with compound names appearing in the Experimental Section.
41. For leading references see, Tomasz, M.; Chawla, A. K.; Lipman, R. Biochemistry 1988, 27, 3182.
42. Antonio, Y.; De La Cruz, M. E.; Galeazzi, E.; Guzman, A.; Bray, B. L.; Greenhouse, R.; Kurz, L. J.; Lustig, D. A.; Maddox, M. L.; Muchowski, J. M. Can. J. Chem. 1994, 72, 15.
43. Bowman, W. R.; Heaney, H.; Jordan, B. M. Tetrahedron 1991, 47, 10119.
44. Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051.
45. The heads of arrows in Figure 1 are the observed hydrogen atoms; the tails are irradiated.
46. Harran, P. G., Ph. D. Thesis, Yale University, 1995.
47. For an example of nucleophilic oxygen capture by an iminium salt during oxidation see, Bartlett, M. F.; Lambert, B. F.; Taylor, W. I. J. Am. Chem. Soc. 1964, 86, 729.
48. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
49. Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D. J. Chem. Soc., Chem. Commun. 1987, 1625.
50. Griffith, W. P.; Ley, S. V. Aldrichim. Acta 1990, 23, 13.
51. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 43, 4155.
52. )For a recent modification of the original procedure and an understanding of the mechanism see, Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
53. Ziegler, F. E.; Wallace, O. B. J. Org. Chem. 1995, 60, 3626.
54. Leonard, N. J.; Miller, L. A.; Thomas, P. D. J. Am. Chem. Soc. 1956, 78, 3463.
55. Stork, G.; Guthikonda, R. N. J. Am. Chem. Soc. 1972, 94, 5109.
56. Magnus, P.; Giles, M.; Bonnert, R.; Johnson, G.; McQuire, L.; Deluca, M.; Merritt, A.; Kim, C. S.; Vicker, N. J. Am. Chem. Soc. 1993, 115, 8116.
57. Ziegler, F. E.; Bennett, G. B. J. Am. Chem. Soc. 1973, 95, 7458.
58. Danishefsky, S. J.; Feigelson, G. B. Heterocycles 1987, 25, 301.
59. Grierson, D. In Organic Reactions; L. A. Paquette, Ed.; John Wiley: New York, 1990; Vol. 39, p 85.
60. All the sec- and tert-carbinolamines encountered in this study were mainly single stereoisomers, and no stereochemical assignments were made.
61. An alternative mechanism is the oxidation of the ring-opened ketoamine intermediate that might exist in low concentration.
62. Hootelé, C. Tetrahedron Lett. 1969, 2713.
63. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
64. Farina, V.; Huang, S. Tetrahedron Lett. 1992, 33, 3979.
65. Otera, J.; Dan-oh, N.; Nozaki, H. J. Org. Chem. 1991, 56, 5307.
66. This ratio varied between 8:1 and 13:1.
67. 7, was not determined.
68. Baggiolini, E.; Hamlow, H. P.; Schaffner, K. J. Am. Chem. Soc. 1970, 92, 4906.
69. For a recent synthetic application of photodecarbonylation see, MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391.
70. Walborsky, H. M.; Allen, L. E. J. Am. Chem. Soc. 1971, 93, 5465.
71. 2RhCl(CO), the product of decarbonylation, has been described: O'Connor, J. M.; Ma, J. Inorg. Chem. 1993, 32, 1866.
72. 3RhCl see, Tsuji, J.; Ohno, K. Synthesis 1969, 157.
73. The decarbonylation conditions reported in the Experimental Section were inconsistently reproducible.
74. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
75. 2O), 3.59 (s, 3 H), 3.45 (d, J = 12.4 Hz, 1 H), 3.32 (dd, J = 4.4, 1.8 Hz, 1 H, NCHCKNBoc), 2.78-2.74 (m, 2 H), 1.22 (s, 9 H), 1.04 (s, 9 H), 0.20 (s, 3H), 0.15(s, 3 H).