Nitrogen-containing tricyclic and tetracyclic compounds by stereoselective samarium diiodide promoted cyclizations of quinolyl-substituted ketones - A new access to azasteroids

European Journal of Organic Chemistry

Volumn , Issue 13, 2008, Pages 2325-2335

  Aulenta, Francesca ^a,b   Wefelscheid, Ulrike K ^a   Brüdgam, Irene ^a   Reißig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b BASF SE   (Germany)

Author keywords

C C coupling; Electron transfer; Quinolines; Samarium; Steroids

Indexed keywords

EID: 52449094352     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800019     Document Type: Article

References (75)

1. a) R. W. Chesnut, N. N. Durham, R. A. Brown, E. A. Mawdsley, K. D. Berlin, Steroids 1976, 27, 525-541;
2. b) R. E. Dolle, H. S. Allaudeen, L. I. Kruse, J. Med. Chem. 1990, 33, 877-880;
3. c) C. Lange, N. Holzhey, B. Schönecker, R. Beckert, U. Möllmann, H.-M. Dahse, Bioorg. Med. Chem. 2004, 12, 3357-3362.
4. For selected examples, see: a) F. Cachoux, M. Ibrahim-Ouali, M. Santelli, Tetrahedron Lett. 2001, 42, 843-845;
5. b) K. Oumzil, M. Ibrahim-Ouali, M. Santelli, Synlett 2005, 1695-1698;
6. c) H. W. Sünnemann, A. Hofmeister, J. Magull, A. de Meijere, Chem. Eur. J. 2006, 12, 8336-8344;
7. d) A. Jacob von Wangelin, H. Neumann, D. Gordes, S. Huber, C. Wendler, S. Klaus, D. Strubing, A. Spannenberg, H. J. Jiao, L. El Firdoussi, K. Thurow, N. Stoll, M. Beller, Synthesis 2005, 2029-2038.
8. a) C. U. Dinesh, H.-U. Reißig, Angew. Chem. 1999, 111, 874-876;
9. Angew. Chem. Int. Ed. 1999, 38, 789-791;
10. b) E. Nandanan, C. U. Dinesh, H.-U. Reißig, Tetrahedron 2000, 56, 4267-4277;
11. c) M. Berndt, H.-U. Reißig, Synlett 2001, 1290-1291;
12. d) S. Gross, H.-U. Reißig, Synlett 2002, 2027-2030;
13. e) S. Gross, H.-U. Reißig, Org. Lett. 2003, 5, 4305-4307;
14. f) M. Berndt, I. Hlobilová, H.-U. Reißig, Org. Lett. 2004, 6, 957-960;
15. g) V. Blot, H.-U. Reißig, Eur. J. Org. Chem. 2006, 4989-4992;
16. h) V. Blot, H.-U. Reißig, Synlett 2006, 2763-2766;
17. i) F. Aulenta, M. Berndt, I. Brüdgam, H. Hartl, S. Sörgel, H.-U. Reißig, Chem. Eur. J. 2007, 13, 6047-6062;
18. j) U. K. Wefelscheid, H.-U. Reißig, Adv. Synth. Catal. 2008, 350, 65-69.
19. For related aryl carbonyl couplings, see: a) H. Ohno, S. Maeda, M. Okumura, R. Wakayama, T. Tanaka, Chem. Commun. 2002, 316-317;
20. b) H. Ohno, R. Wakayama, S. Maeda, H. Iwasaki, M. Okumura, C. Iwata, H. Mikamiyama, T. Tanaka, J. Org. Chem. 2003, 68, 5909-5916;
21. c) H. Ohno, M. Okumura, S. Maeda, H. Iwasaki, R. Wakayama, T. Tanaka, J. Org. Chem. 2003, 68, 7722-7732;
22. d) C.-W. Kuo, J.-M. Fang, Synth. Commun. 2001, 31, 877-892;
23. e) J.-S. Shiue, M.-H. Lin, J.-M. Fang, J. Org. Chem. 1997, 62, 4643-4649;
24. f) H.-G. Schmalz, S. Siegel, J. W. Bats, Angew. Chem. 1995, 107, 2597-2599;
25. Angew. Chem. Int. Ed. Engl. 1995, 34, 2383-2385.
26. Selected reviews dealing with samarium-promoted reactions: a) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307-338;
27. b) F. A. Khan, R. Zimmer, J. Prakt. Chem. 1997, 339, 101-104;
28. c) G. A. Molander, C. R. Harris, Tetrahedron 1998, 54, 3321-3354;
29. d) A. Krief, A.-M. Laval, Chem. Rev. 1999, 99, 745-777;
30. e) H. B. Kagan, J. L. Namy in Topics in Organometallic Chemistry Vol. 2: Lanthanides - Chemistry and Use in Organic Synthesis (Ed.: S. Kobayashi), Springer, Berlin, 1999, pp. 155-198;
31. f) P. G. Steel, J. Chem. Soc. Perkin Trans. 1 2001, 2727-2751;
32. g) A. Hölemann, Synlett 2001, 1497-1498;
33. h) B. K. Banik, Eur. J. Org. Chem. 2002, 2431-2444;
34. i) H. B. Kagan, Tetrahedron 2003, 59, 10351-10372;
35. j) M. Berndt, S. Gross, A. Hölemann, H.-U. Reißig, Synlett 2004, 422-438;
36. k) D. J. Edmonds, D. Johnston, D.-J. Procter, Chem. Rev. 2004, 104, 3371-3404;
37. l) J. M. Concellón, H. Rodriguez-Solla, Chem. Soc. Rev. 2004, 33, 599-609.
38. 2 and it is required for many ketyl-coupling reactions, see: a) E. Prasad, R. A. Flowers II, J. Am. Chem. Soc. 2002, 124, 6895-6899;
39. b) J. Inanaga, M. Ishikawa, M. Yamaguchi, Chem. Lett. 1987, 1485-1486.
40. a) D. C. Spellmeyer, K. N. Houk, J. Org. Chem. 1987, 52, 959-974;
41. b) A. L. J. Beckwith, Tetrahedron 1981, 37, 3073-3100.
42. a) T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 1971, 44, 581-581;
43. b) R. F. Heck, J. P. Nolley Jr., J. Org. Chem. 1972, 37, 2320-2322;
44. c) Selected Reviews: I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066;
45. d) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 345-390;
46. e) A. de Meijere, F. E. Meyer, Angew. Chem. 1994, 106, 2473-2506;
47. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379-2411;
48. for a scope of reaction conditions, see: f) S. Bräse, A. de Meijere, "Cross-Coupling of Organyl Halides with Alkenes: The Heck Reaction" in Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 1998, ch. 3;
49. g) R. F. Heck, Comprehensive Organic Synthesis (Ed.: B. M. Trost), Pergamon, New York, 1991, vol. 4, ch. 4.3.
50. F. Aulenta, H.-U. Reißig, Synlett 2006, 2993-2996.
51. For a previous synthesis of nonaflate 14, see: A. G. Martinez, A. H. Fernandez, R. M. Alvarez, Synthesis 1984, 481-485.
52. a) G. P. Roth, C. E. Fuller, J. Org. Chem. 1991, 56, 3493-3496;
53. b) M. Rottländer, P. Knochel, J. Org. Chem. 1998, 63, 203-208;
54. c) S. E. Denmark, R. F. Sweis, Org. Lett. 2002, 4, 3771-3774;
55. d) O. Flögel, J. Dash, I. Brüdgam, H. Hartl, H.-U. Reißig, Chem. Eur. J. 2004, 10, 4283-4290;
56. e) A. Gavryushin, C. Kofink, G. Manolikakes, P. Knochel, Org. Lett. 2005, 7, 4871-4874;
57. f) R. E. Tundel, K. W. Anderson, S. L. Buchwald, J. Org. Chem. 2006, 71, 430-433;
58. g) J. Dash, T. Lechel, H.-U. Reißig, Org. Lett. 2007, 9, 5541-5544.
59. L. R. Subramanian, H. Bentz, M. Hanack, Synthesis 1973, 293-294.
60. A. Padwa, A. Zanka, J. M. Harris, Tetrahedron 2003, 59, 4939-4944.
61. For the synthesis of 20 see: D. Tobia, B. Rickborn, J. Org. Chem. 1989, 54, 777-782.
62. J. R. Parikh, W. v. E. Doering, J. Am. Chem. Soc. 1967, 89, 5505-5507.
63. For example: a) T. Jeffery, J. Chem. Soc., Chem. Commun. 1984, 1287-1289;
64. b) T. Jeffery, Tetrahedron Lett. 1985, 26, 2667-2670;
65. c) S.-K. Kang, K.-Y. Jung, C.-H. Park, E.-Y. Namkoong, T.-H. Kim, Tetrahedron Lett. 1995, 36, 6287-6290;
66. d) E. C. Taylor, Y. Wang, Heterocycles 1998, 48, 1537-1553;
67. [13]
68. F. Aulenta, A. Hölemann, H.-U. Reißig, Eur. J. Org. Chem. 2006, 1733-1739.
69. [4a,4b]
70. D. Marcovici-Mizrahi, H. E. Gottlieb, V. Marks, A. Nudelman, J. Org. Chem. 1996, 61, 8402-8406.
71. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
72. For a review dealing with directed dihydroxylation reactions see: T. J. Donohoe, Synlett 2002, 1223-1232.
73. Remarkably, compound 32 slowly isomerized by standing in deuterated methanol into an isomer with very similar spectroscopic data. The structure of this compound and the mechanism of its formation could not unambiguously be established so far. Experiments dealing with this observation are in progress.
74. Compound 27 showed a high affinity towards the estrogenic receptor at 1μM concentration: I. Ott, R. Gust, Institut für Pharmazie der Freien Universität Berlin, unpublished results.
75. Two distinct rotamers were visible in the NMR spectroscopic analysis performed at room temperature.