Synthesis of (±)-aphanorphine: a new approach to tricyclic 3-benzazepine scaffold using two radical C-C bond-forming reactions

Tetrahedron Letters

Volumn 49, Issue 29-30, 2008, Pages 4473-4475

  Yoshimitsu, Takehiko ^a   Atsumi, Chie ^a   Iimori, Emiko ^b   Nagaoka, Hiroto ^b   Tanaka, Tetsuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

^b MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMOANISALDEHYDE; 3 BENZAZEPINE DERIVATIVE; ALDEHYDE DERIVATIVE; APHANORPHINE; N METHYLPYRROLIDONE; PYRROLIDINE DERIVATIVE;

ANNULATION REACTION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DEMETHYLATION; DRUG SYNTHESIS;

EID: 44949109025     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.058     Document Type: Article

References (73)

1. Gulavita N., Hori A., Shimizu Y., Laszlo P., and Clardy J. Tetrahedron Lett. 29 (1988) 4381-4384
2. Total and formal syntheses:. Takano S., Inomata K., Sato T., and Ogasawara K. J. Chem. Soc., Chem. Commun. (1989) 1591-1592
3. Takano S., Inomata K., Sato T., Takahashi M., and Ogasawara K. J. Chem. Soc., Chem. Commun. (1990) 290-292
4. Honda T., Yamamoto A., Cui Y., and Tsubuki M. J. Chem. Soc., Perkin Trans. 1 (1992) 531-532
5. Meyers A.I., Schmidt W., and Santiago B. Heterocycles 40 (1995) 525-529
6. Hulme A.N., Henry S.S., and Meyers A.I. J. Org. Chem. 60 (1995) 1265-1270
7. Hallinan K.O., and Honda T. Tetrahedron 51 (1995) 12211-12216
8. Fadel A., and Arzel P. Tetrahedron: Asymmetry 6 (1995) 893-900
9. Node M., Imazato H., Kurosaki R., Kawano Y., Inoue T., Nishide K., and Fuji K. Heterocycles 42 (1996) 811-819
10. Shiotani S., Okada H., Nakamata K., Yamamoto T., and Sekino F. Heterocycles 43 (1996) 1031-1047
11. Shimizu M., Kamikubo T., and Ogasawara K. Heterocycles 46 (1997) 21-26
12. Fadel A., and Arzel P. Tetrahedron: Asymmetry 8 (1997) 283-291
13. Fadel A., and Arzel P. Tetrahedron: Asymmetry 8 (1997) 371-374
14. Tanaka K., Taniguchi T., and Ogasawara K. Tetrahedron Lett. 42 (2001) 1049-1052
15. Tamura O., Yanagimachi T., Kobayashi T., and Ishibashi H. Org. Lett. 3 (2001) 2427-2429
16. Fuchs J.R., and Funk R.L. Org. Lett. 3 (2001) 3923-3925
17. ElAzab A.S., Taniguchi T., and Ogasawara K. Heterocycles 56 (2002) 39-43
18. Tamura O., Yanagimachi T., and Ishibashi H. Tetrahedron: Asymmetry 14 (2003) 3033-3041
19. Zhai H., Luo S., Ye C., and Ma Y. J. Org. Chem. 68 (2003) 8268-8271
20. Taylor S.K., Ivanovic M., Simons L.J., and Davis M.M. Tetrahedron: Asymmetry 14 (2003) 743-747
21. Kita Y., Futamura J., Ohba Y., Sawama Y., Ganesh J.K., and Fujioka H. J. Org. Chem. 68 (2003) 5917-5924
22. Hu H., and Zhai H. Synlett (2003) 2129-2130
23. Bower J.F., Szeto P., and Gallagher T. Chem. Commun. (2005) 5793-5795
24. Katoh M., Inoue H., Suzuki A., and Honda T. Synlett (2005) 2820-2822
25. Li M., Zhou P., and Roth H.F. Synthesis (2007) 55-60
26. Ma Z., and Zhai H. Synlett (2007) 161-163
27. Bower J.F., Szeto P., and Gallagher T. Org. Biomol. Chem. 5 (2007) 143-150
28. Ma Z., Hu H., Xiong W., and Zhai H. Tetrahedron 63 (2007) 7523-7531
29. Grainger R.S., and Welsh E.J. Angew. Chem., Int. Ed. 46 (2007) 5377-5380
30. Yoshimitsu T., Arano Y., and Nagaoka H. J. Am. Chem. Soc. 127 (2005) 11610-11611
31. For reviews, see:. Yoshimitsu T., Nagaoka H., and Tanaka T. J. Synth. Org. Chem. Jpn. 65 (2007) 665-675
32. Yoshimitsu T. Farumashia 43 (2007) 219-223
33. 3C-H carbamoylation:. Yoshimitsu T., Matsuda K., Nagaoka H., Tsukamoto K., and Tanaka T. Org. Lett. 9 (2007) 5115-5118
34. Reviews of alpha-aminoalkyl radical chemistry:. Aurrecoechea J.M., and Suero R. ARKIVOC (2004) 10-35
35. Hart D. In: Renaud P., and Sibi M.P. (Eds). Radicals in Organic Synthesis Vol. 2 (2001), Wiley-VCH, Weinheim, Germany 279-302
36. Renaud P., and Giraud L. Synthesis (1996) 913-926
37. Pertinent reviews of alpha-functionalization of nitrogen compounds, see:. Campos K.R. Chem. Soc. Rev. 36 (2007) 1069-1084
38. Griesbeck A.G., Hoffmann N., and Warzecha K.-d. Acc. Chem. Res. 40 (2007) 128-140
39. Hoffmann N., Bertrand S., Marinkovic S., and Pesch J. Pure Appl. Chem. 78 (2006) 2227-2246
40. Ishii Y., and Sakaguchi S. Bull. Chem. Soc. Jpn. 77 (2004) 909-920
41. Beak P., Johnson T.A., Kim D.D., and Lim S.H. Top. Organomet. Chem. 5 (2003) 139
42. Doye S. Angew. Chem., Int. Ed. 40 (2001) 3351
43. 3C-H transformation, see:. Hartwig J.F., and Seth B.H. J. Am. Chem. Soc. 129 (2007) 6690
44. Li Z., Bohle D.S., and Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 8928
45. Campos K.R., Klapars A., Waldman J.H., Dormer P.G., and Chen C.-y. J. Am. Chem. Soc. 128 (2006) 3538-3539
46. Pastine S.J., Gribkov D.V., and Sames D. Am. Chem. Soc. 128 (2006) 14220-14221
47. Catino A.J., Nichols J.M., Nettles B.J., and Doyle M.P. J. Am. Chem. Soc. 128 (2006) 5648-5649
48. Matsuo J., Tanaki Y., and Ishibashi H. Org. Lett. 8 (2006) 4371-4374
49. Li Z., and Li C.-J. J. Am. Chem. Soc. 127 (2005) 3672-3673
50. Li Z., and Li C.-J. Eur. J. Org. Chem. 15 (2005) 3173-3176
51. Li Z., and Li C.-J. J. Am. Chem. Soc. 126 (2004) 11810-11811
52. Li Z., and Li C.-J. Org. Lett. 6 (2004) 4997-4999
53. DeBoef B., Pastine S.J., and Sames D. J. Am. Chem. Soc. 126 (2004) 6556-6557
54. Murahashi S.-i., Komiya N., Terai H., and Nakase T. J. Am. Chem. Soc. 125 (2003) 15312-15313
55. Davies H.M.L., Venkataramani C., Hansen T., and Hopper D.W. J. Am. Chem. Soc. 125 (2003) 6462-6468
56. Davies H.M.L., and Venkataramani C. Angew. Chem., Int. Ed. 41 (2002) 2197-2199
57. Suga S., Suzuki S., and Yoshida J. J. Am. Chem. Soc. 124 (2002) 30-31
58. Yoshida J., Suga S., Suzuki S., Kinomura N., Yamamoto A., and Fujiwara K. J. Am. Chem. Soc. 121 (1999) 9546-9549
59. Chatani N., Asaumi T., Yorimitsu S., Ikeda T., Kakiuchi F., and Murai S. J. Am. Chem. Soc. 123 (2001) 10935-10941
60. Chatani N., Fukuyama T., Tatamidani H., Kakiuchi F., and Murai S. J. Org. Chem. 65 (2000) 4039-4047
61. Marinkovic S., and Hoffmann N. Chem. Commun. (2001) 1576-1578
62. Lear Y., and Durst T. Can. J. Chem. 75 (1997) 817
63. Comins D.L., and Brown J.D. J. Org. Chem. 49 (1984) 1078-1083
64. Ollivier C., and Renaud P. Chem. Rev. 101 (2001) 3415-3434
65. Yorimitsu H., and Oshima K. In: Renaud P., and Sibi M.P. (Eds). Radicals in Organic Synthesis Vol. 1 (2001), Wiley-VCH, Weinheim, Germany 11-27
66. O'Mahony G. Synlett (2004) 572-573
67. Yamamoto, Y. (original commentary); Yoshimitsu, T. (first update); Wood, J. L.; Schacherer, L. N. (second update) In e-EROS Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A.; Fuchs, P. L.; Wipf, P.; Crich, D. Eds.; Wiley, 2007.
68. 3SnH/AIBN-mediated reduction of major 3a provided a debrominated alcohol that was identical to the authentic material whose structure was unambiguously elucidated by X-ray analysis.
69. For instance, an attempt to methylenate lactam 6 by a three-step procedure involving (1) ethoxylation, (2) hydroxymethylation with paraformaldehyde, and (3) deacylation was unsuccessful in our hands:. Rigolet S., Melot J.M., Vebrel J., Chiaroni A., and Riche C. J. Chem. Soc., Perkin Trans. 1 (2000) 1095-1103
70. Klutchko S., and Hoefle M.L. J. Med. Chem. 24 (1981) 104-109
71. Yang J., Cohn S.T., and Romo D. Org. Lett. 6 (2000) 763-766
72. Superiority of ACCN compared to AIBN, for example, see:. Keck G.E., and Burnett D.A. J. Org. Chem. 52 (1987) 2960-2962
73. 3) δ 21.5, 35.7, 41.5, 41,7, 43.2, 55.2, 61.2, 71.3, 109.4, 110.8, 126.1, 130.2, 148.1, 157.7. (±)-Aphanorphine (1) (Refs. 2n, 2o, and 2x)