Concise syntheses of (-)-galanthamine and (±)-codeine via intramolecular alkylation of a phenol derivative

Journal of the American Chemical Society

Volumn 131, Issue 44, 2009, Pages 16045-16047

  Magnus, Philip ^a   Sane, Neeraj ^a   Fauber, Benjamin P ^a   Lynch, Vince ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[60] FULLERENE; BULK-HETEROJUNCTION STRUCTURE; CONCISE SYNTHESIS; GALANTHAMINE; I-LAYER; INTRAMOLECULAR ALKYLATION; NEW SOLUTIONS; P-LAYER; PHENOL DERIVATIVES; PHOTOVOLTAIC DEVICES; POWER CONVERSION EFFICIENCIES; PROCESSABLE; TETRABENZOPORPHYRINS;

CONVERSION EFFICIENCY; CRYSTAL STRUCTURE; FULLERENES; HYDROCARBONS; PHENOLS;

HETEROJUNCTIONS;

CODEINE; GALANTAMINE; PHENOL DERIVATIVE;

ALKYLATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IN VIVO STUDY; SUZUKI REACTION; TEMPERATURE MEASUREMENT;

ALKYLATION; CODEINE; GALANTAMINE; PHENOLS;

EID: 70450173919     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9085534     Document Type: Article

References (73)

1. Isolation:Proskurnina, N. F.; Yakovleva, A. P. Russ. J. Gen. Chem. 1952, 22, 1941-1944.
2. Structure: Kobayashi, S.; Shingu, T.; Uyeo, S. Chem. Ind. 1956, 177-178.
3. Rainer, M. CNS Drugs 1997, 7, 9-97.
4. Rainer, M.; Mucke, H. A. M. Intl. J. Geriatric Psychopharmacol. 1998, 1, 197-201.
5. (a) Barton, D. H. R.; Kirby, G. W. Proc. Chem. Soc. 1960, 392-393.
6. (b) Barton, D. H. R.; Kirby, G. W. J. Chem. Soc. 1962, 806-817.
7. (c) Kametani, T.; Yamaki, K.; Yagi, H.; Fukumoto, K. Chem. Commun. 1969, 425-426.
8. (d) Kametani, T.; Yamaki, K.; Yagi, H.; Fukumoto, K. J. Chem. Soc. C 1969, 2602-2605.
9. (e) Kametani, T.; Seino, C.; Yamaki, K.; Shibuya, S.; Fukumoto, K.; Kigasawa, K.; Satoh, F.; Hiiragi, M.; Hayasaka, T. J. Chem. Soc. C 1971, 1043-1047.
10. (f) Kametani, K.; Shishido, K.; Hayashi, E.; Seino, C.; Kohno, T.; Shibuya, S.; Fukumoto, K. J. Org. Chem. 1971, 36, 1295-1297.
11. (g) Shimizu, K.; Tomioka, K.; Yamada, S.; Koga, K. Chem. Pharm. Bull. 1978, 26, 3765-3771.
12. (h) Chaplin, D. A.; Fraser, N.; Tiffin, P. D. Tetrahedron Lett. 1997, 38, 7931-7932.
13. (i) Czollner, L.; Frantsits, W.; Küenburg, B.; Hedenig, U.; Fröehlich, J.; Jordis, U. Tetrahedron Lett. 1998, 39, 2087-2088.
14. (j) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625-6633.
15. (k) Küenburg, B.; Czollner, L.; Fröehlich, J.; Jordis, U. Org. Process Res. Dev. 1999, 3, 425-431.
16. (l) Krikorian, D.; Tarpanov, V.; Parushev, S.; Mechkarova, P. Synth. Commun. 2000, 30, 2833-2846.
17. (m) Node, M.; Kodama, S.; Hamashima, Y.; Baba, T.; Hamamichi, N.; Nishide, K. Angew. Chem., Int. Ed. 2001, 40, 3060-3062.
18. (n) Kodama, S.; Hamashima, Y.; Nishide, K.; Node, M. Angew. Chem., Int. Ed. 2004, 43, 2659-2661.
19. (a) Pilger, C.; Westermann, B.; Flörke, U.; Fels, G. Synlett 2000, 1163-1165.
20. (b) Guillou, C.; Beunard, J.-L.; Gras, E.; Thal, C. Angew. Chem., Int. Ed. 2001, 40, 4745-4746.
21. (c) Trost, B. M.; Tang, W.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 14785-14804.
22. (a) Krikorian, D.; Vlahov, R.; Parrushev, S.; Chinova, M.; Vlahov, I.; Schafer, H.-J.; Duddeck, H.; Snatzke, G. Tetrahedron Lett. 1984, 25, 2969-2972.
23. (b) Holton, R. A.; Sibi, M. P.; Murphy, W. S. J. Am. Chem. Soc. 1988, 110, 314-316.
24. (c) Szewczyk, J.; Lewin, A. H.; Carroll, F. I. J. Heterocycl. Chem. 1988, 25, 1809-1811.
25. (d) Vlahova, R.; Krikorian, D.; Spassov, G.; Chinova, M.; Vlahov, I.; Parushev, S.; Snatzke, G.; Ernst, L.; Kieslich, K.; Abraham, W.-R.; Sheldrick, W. S. Tetrahedron 1989, 45, 3329-3345.
26. (e) Szewczyk, J.; Wilson, J. W.; Lewin, A. H.; Carroll, F. I. J. Heterocycl. Chem. 1995, 32, 195-199.
27. (f) Parsons, P. J.; Charles, M. D.; Harvey, D. M.; Sumoreeah, L. R.; Shell, A.; Spoors, G.; Gill, A. L.; Smith, S. Tetrahedron Lett. 2001, 42, 2209-2211.
28. (g) Hu, X.-D.; Tu, Y. Q.; Zhang, E.; Gao, S.; Wang, S.; Wang, A.; Fan, C.-A.; Wang, M. Org. Lett. 2006, 8, 1823-1825.
29. (h) Node, M.; Kodama, S.; Hamashima, Y.; Katoh, T.; Nishide, K.; Kajimoto, T. Chem. Pharm. Bull. 2006, 54, 1662-1679.
30. (i) Tanimoto, H.; Kato, T.; Chida, N. Tetrahedron Lett. 2007, 48, 6267-6270.
31. (j) Satcharoen, V.; McLean, N. J.; Kemp, S. C.; Camp, N. P.; Brown, R. C. D. Org. Lett. 2007, 9, 1867-1869.
32. Shieh, W.-C.; Carlson, J. A. J. Org. Chem. 1994, 59, 5463-5465.
33. Gulland, J. M.; Robinson, R. Mem. Proc. Manchester Lit. Phil. Soc. 1925, 69, 79-85.
34. For total and formal syntheses of morphine and morphine-like alkaloids: (a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109-1110.
35. (b) Elad, D.; Ginsburg, D. J. Am. Chem. Soc. 1954, 76, 312-313.
36. (c) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1956, 78, 1380-1393.
37. (d) Barton, D. H. R.; Kirby, G. W.; Steglich, W.; Thomas, G. M. Proc. Chem. Soc. 1963, 203-204.
38. (e) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. C 1969, 2030-2033.
39. (f) Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239-1240.
40. (g) Iijima, I.; Minamikawa, J.; Jacobson, A. E.; Rice, K. C. J. Org. Chem. 1978, 43, 1462-1463.
41. (h) Lie, T. S.; Maat, H. C.; Beyerman, H. C. Recl. Trav. Chim. Pays-Bas. 1979, 98, 419-420.
42. (i) Moos, W. H.; Gless, R. D.; Rapoport, H. J. Org. Chem. 1983, 48, 227-238.
43. (j) White, J. D.; Caravatti, G.; Kline, T. B.; Edstrom, E.; Rice, K. C.; Brossi, A. Tetrahedron 1983, 39, 2393-2397.
44. (k) Ludwig, W.; Schäfer, H. J. Angew. Chem., Int. Ed. 1986, 25, 1025-1026.
45. (l) Toth, J. E.; Fuchs, P. L. J. Org. Chem. 1987, 52, 473-475.
46. (m) Schwartz, M. A.; Pham, P. T. K. J. Org. Chem. 1988, 53, 2318-2322.
47. (n) Tius, M. A.; Kerr, M. A. J. Am. Chem. Soc. 1992, 114, 5959-5966.
48. (o) Parker, K. A.; Fokas, D. J. Am. Chem. Soc. 1992, 114, 9688-9689.
49. (p) Hong, C. H.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028-11029.
50. (q) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3933-3938.
51. (r) Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927-3933.
52. (s) Mulzer, J.; Duerner, G.; Trauner, D. Angew. Chem., Int. Ed. 1997, 35, 2830-2832.
53. (t) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1997, 62, 5250-5251.
54. (u) Trauner, D.; Porth, S.; Opatz, T.; Bats, J. W.; Giester, G.; Mulzer, J. Synthesis 1998, 653-664.
55. (v) Mulzer, J.; Trauner, D. Chirality 1999, 11, 475-482.
56. (w) Nagata, H.; Miyazawa, N.; Ogasawara, K. Chem. Commun. 2001, 1094-1095.
57. (x) Taber, D. F.; Neubert, T. D.; Rheingold, A. L. J. Am. Chem. Soc. 2002, 124, 12416-12417.
58. (y) Uchida, K.; Yokoshima, S.; Kan, T.; Fukuyama, T. Org. Lett. 2006, 8, 5311-5313.
59. (z) Zezula, J.; Rice, K. C.; Hudlicky, T. Synlett 2007, 2863-2867.
60. Omori, A. T.; Finn, K. J.; Leisch, H.; Carroll, R. J.; Hudlicky, T Synlett 2007, 2859-2862.
61. (aa) Stork, G.; Yamashita, A.; Adams, J.; Schulte, G. R.; Chesworth, R.; Miyazaki, Y.; Farmer, J. G J. Am. Chem. Soc. 2009, 131, 11402-11406.
62. For recent reviews see: (a). Hudlicky, T.; Butora, G.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R. Stereoselective Synthesis (Part K); Rahman, A., Ed.; Studies in Natural Products Chemistry, Vol 18; Elsevier: New York, 1996; pp 43-154.
63. (b) Blakemore, P. R.; White, J. D. Chem. Commun. 2002, 1159-1168.
64. (c) Hudlicky, T.; Zezula, J. Synlett 2005, 388-405.
65. Grewe, R.; Fischer, H.; Friedrichsen, W. Chem. Ber. 1967, 100, 1-8.
66. Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550-1558.
67. Rice, K. C. J. Org. Chem. 1980, 45, 3135-3137.
68. Barton, D. H. R.; Cohen, T. Festschr. Arthur Stoll 1957, 117-143.
69. Barton, D. H. R.; Kirby, G. W.; Steglich, W.; Thomas, G. M.; Battersby, A. R.; Dobson, T. A.; Ramuz, H. J. Chem. Soc. 1965, 2423-2438.
70. Zenk, M. H.; Gerardy, R.; Stadler, R. J. Chem. Soc., Chem. Commun. 1989, 1725-1727.
71. Amann, T.; Zenk, M. H Tetrahedron Lett. 1991, 32, 3675-3678.
72. Gerardy, R.; Zenk, M. H. Phytochemistry 1993, 32, 79-86.
73. Murphy, W. S.; Wattanasin, S. Chem. Soc. Rev. 1983, 213-250.