Toward a practical synthesis of morphine. The first several generations of a radical cyclization approach

Synthesis

Volumn , Issue SPEC. ISS. APR., 1998, Pages 665-681

  Butora, Gabor ^a   Hudlicky, Tomas ^a   Fearnley, Stephen P ^a   Stabile, Michele R ^a   Gum, Andrew G ^a   Gonzalez, David ^a  

^a University of Florida   (United States)

Author keywords

Approach to (+) morphine; Ent morphinans; Enzymatic dioxygenation; Isoquinoline alkaloids; Radical cyclization

Indexed keywords

ISOQUINOLINE ALKALOID; MORPHINE; MORPHINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; OXIDATION; STEREOCHEMISTRY; STEREOISOMERISM; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; STRUCTURE ANALYSIS;

EID: 0031597452     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-5931     Document Type: Article

References (84)

1. For a preliminary account on this work see: Butora, G.; Hudlicky, T.; Fearnley, S.P.; Gum, A.G;. Stabile, M.R; Abboud K.A. Tetrahedron Lett. 1996, 8155.
2. White, P.T.; Raymer, S. "The Poppy," National Geographic Feb. 1985, vol. 167, pp 142-188.
3. See also Rice, K.C. in The Chemistry and Biology of Isoquinoline Alkaloids; Phillipson, et al, Eds.; Springer: Berlin, 1985; pp 191-203.
4. Terry, C.E; Pellens, M. The Opium Problem;
5. Ch. 2, Bur. Soc. Hyg. New York, 1928.
6. U.S. Drug Enforcement Agency, "Controlled Substance Aggregate Production Quota History", Federal Register, July 7, 1994.
7. National Narcotics Intelligence Consumers Committee Report 1993, "The Supplies of Illicit Drugs to the United States", DEA-94066, August 1994.
8. Pollan, M. Harper's Magazine 1997 35, 294.
9. a) Morphine, named after the Greek god of dreams, Morpheus, is one of the oldest drugs on record. The first documented use of opium goes back to 1500 BC and the power of the drug as an analgesic is mentioned in sources as old as Homer's Odyssey and the New Testament.
10. b) The primary medical use of morphine is for the relief of very strong pain, such as that derived from severe wounds, some tumors or major surgery procedures. Because morphine acts on respiratory function in higher doses while maintaining no influence on cardiac activity it is an ideal anesthetic for heart surgery. Derivatives of morphine such as codeine are used as cough suppressants, while antagonists such as naloxone or naltrexone are used in the treatment of accidental overdose. Further chemical manipulation of morphine and other natural opium alkaloids provides a wide family of agonists and antagonists that have become essential in modern medical procedures.
11. Wilson, M.I.; Coscia, C.J. J. Am. Chem. Soc. 1995, 97, 431.
12. Kutney, J.P. Acc. Chem. Res. 1996, 26, 559.
13. Tencheva, Z.S.; Belcheva, M.M.; Coscia, C.J. Mol. Brain Res. 1997, 48, 156.
14. Scheneider, B.; Zenk, M.H. Phytochemistry 1993, 33, 1431.
15. Long, M.T.; Hailes, A.M.; Bruce, N.C. Appl. Environ. Microbiol. 1995, 61, 3645.
16. French, C.E.; Hailes, A.M.; Rathbone, D.A.; Long, M.T.; Willey, D.L.; Bruce, N.C. Biotechnology, 1995, 13, 674.
17. Hailes, A.M.; Bruce, N.L. Appl. Environ. Microbiol., 1993, 59, 2166.
18. Bruce, N.J; French, C.E.; Hailes, A.M; Long, M.T.; Rathbone, D.A. Trends Biotech. 1995, 13, 200.
19. Lenz, R.; Zenk, M.H. Tetrahedron Lett. 1995, 36, 2449.
20. a) Muhtadi, F.J. "Analytical Profile of Morphine" in Analytical Profiles of Drug Substances 1988 77, 259.
21. b) Muhtadi, F.J.; Hassan, M.A. "Codeine Phosphate" in Analytical Profiles of Drug Substances 1981 10, 93.
22. c) Wyatt, D.K.; Grady, L.T. "Heroin" in Analytical Profiles of Drug Substances 1981 10, 357.
23. a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1952, 74, 1109.
24. b) Elad, D.; Ginsburg, D. J. Am, Chem. Soc. 1954, 76, 312.
25. c) Barton, D.H.R.; Kirby, G.W.; Steglich, W.; Thomas, G.M. Proc. Chem. Soc. 1963, 203.
26. d) Grewe, R.; Friedrichsen, W. Chem. Ber. 1967, 100, 1550.
27. e) Morrison, G.C.; Waite, R.O.; Shavel, J., Jr. Tetrahedron Lett. 1967, 4055.
28. f) Kametani, T.; Ihara, M.; Fukumoto, K.; Yagi, H. J. Chem. Soc. (C) 1969, 2030.
29. g) Schwartz, M.A.; Pham, P.T.K. J. Org. Chem. 1988, 53, 2318.
30. h) Lie, T.S.; Maat, L.; Beyerman, H.C. Recl. Trav. Chim. Pays-Bas. 1979, 98, 419.
31. i) Rice, K.C. J. Org. Chem. 1980, 45, 3135.
32. j) Evans, D.A.; Mitch, C.H. Tetrahedron Lett. 1982, 23, 285.
33. k) Moos, W.H.; Gless, R.D.; Rapoport, H. J. Org. Chem. 1983, 48, 227.
34. l) White, J.D.; Caravatti, G.; Kline, T.B.; Edstrom, E.; Rice, K.C.; Brossi, A. Tetrahedron 1983, 39, 2393.
35. m) Ludwig, W.; Schäfer, H.J. Angew., Chem. 1986, 95, 1032;
36. Angew. Chem., Int. Ed. Engl. 1986, 25, 1025.
37. n) Toth, J.E.; Fuchs, P.L. J. Org. Chem. 1987, 52, 473.
38. o) Tius, M.A.; Kerr, M.A. J. Am. Chem. Soc. 1992, 114, 5959.
39. p) Parker, K.A.; Fokas, D. J. Am. Chem. Soc. 1992, 114, 9688.
40. r) Hong, C.Y.; Kado, N.; Overman, L.E. J. Am. Chem. Soc. 1993, 115, 11028.
41. s) Mulzer, J.; Durner, G.; Trauner, D. Angew. Chem. 1996, 108, 3046;
42. Angew. Chem., Int. Ed. Engl. 1996, 35, 2830.
43. a) Hudlicky, T.; Butora, G.; Fearnley, S.P.; Gum, A.G.; Stabile, M.R. Studies in Natural Product Chemistry 1996, 18, 43.
44. b) Maier, M. Synthesis of Morphine in Organic Synthesis Highlights II Waldman, H.; Ed.; VCH: Weinheim, 1995, pp 357-369.
45. See ref. 9a for the list of approaches and dissertations dealing with morphine synthesis.
46. Hudlicky, T.; Boros, C.H.; Boros, E.E. Synthesis 1992, 174.
47. Butora, G.; Gum, A.G.; Hudlicky, T.; Abboud, K.A. Synthesis 1998, 275.
48. For reviews on Cascade or "Domino" reactions see Tietze, L.F.; Beifuss, U. Angew. Chem., 1993, 105, 137;
49. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
50. a) Stabile, M.R.; Hudlicky, T.; Meiseis, M.L. Tetrahedron: Asymmetry 1995, 6, 537.
51. b) Stabile, M.R.; Hudlicky, T.; Meiseis, M.L.; Butora, G.; Gum, A.G.; Fearnley, S.P.; Thorpe, A.J.; Ellis, M.R. Chirality 1995, 7, 556.
52. Gibson, D.T. Science 1968, 161, 1093.
53. Gibson, D.T.; Hensley, M.; Yoshioka, H.; Mabry, T. J. Biochemistry 1970, 9, 1626.
54. Zylstra, G.J.; Gibson, D.T. J. Biol. Chem. 1989, 264, 14940.
55. Hudlicky, T.; Endoma, M.A.E.; Butora, G. J. Chem. Soc., Perkin 1 1996, 2187.
56. For comprehensive reviews of arene cis-diol chemistry see: Brown, S.M.; Hudlicky, T. In Organic Synthesis: Theory and Applications; Vol 2; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; p. 113.
57. Widdowson, D.A.; Ribbons, D.W.; Thomas, S.D. Janssen Chimica Acta 1990, 8, 3.
58. Carless, H.A.J. Tetrahedron: Asymmetry 1992, 3, 795.
59. Hudlicky, T.; Reed, J. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; p. 271.
60. Grund, A.D. SIM News 1995, 45, 59.
61. Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment, ACS Symposium Series; Vol. 626; Anastas, P.T.; Williamson, T., Eds.; Washington, DC, 1996; p. 180.
62. Hudlicky, T.; Thorpe, A.J. J. Chem. Soc., Chem Commun. 1996, 1993.
63. Hudlicky, T. Chem. Rev., 1996, 96, 3.
64. Hudlicky, T.; Entwistle, D.A.; Pitzer, K.K.; Thorpe, A.J. Chem. Rev. 1996, 96, 1195.
65. Nicolaou, K.; Sorensen, E.; Hwang, C.-K.; Discordia, R.; Bergman, R.; Minto, R. U. S. Patent 5183942.
66. Sakai, Y.; Nishiwaki, E.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1991, 32, 4363.
67. Nicolaou, K.; Zuccarello, G.; Ogawa, Y.; Schweiger, E.; Kumaa, T. J. Am. Chem. Soc. 1992, 110, 4866.
68. Jones, R.; Bergman, R. J. Am. Chem. Soc. 1972, 94, 660.
69. Nicolaou, K.; Zuccarello, G.; Riemer, C.; Estevez, V.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 7361.
70. Semmelhack, M.; Gallagher, J. Tetrahedron Lett. 1993, 34, 4121.
71. Vollhardt, P.; Winn, L. Tetrahedron Lett. 1985, 26, 709.
72. Namy, J.; Souppe, J.; Kagan, J. Tetrahedron Lett. 1983, 24, 765.
73. Vollhardt, P.; Berries, B. Tetrahedron 1982, 19, 2911.
74. For a review see: Block, E. Org. React. 1984, 30, 457.
75. For a review see: Paquette, L. Org. React. 1977, 25, 1.
76. David, S.; Hanessian, S. Tetrahedron 1985, 41, 643.
77. Hudlicky, T.; Stabile, M.R.; Gibson, D.T.; Whited, G.M. Org. Syn. 1998, 76, in press.
78. Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877.
79. Mitsunobu, O. Synthesis 1981, 1.
80. Huges D.L., Org. React. 1992, 42, 335.
81. Mitsunobo, O.; Jenkins, I.D. in Encyclopedia of Reagents for Organic Synthesis, Paquette, L.A., Ed.; Wiley: New York, 1995; Vol. 8, pp. 5379.
82. Hudlicky, T.; Boros, C.H. Tetrahedron Lett. 1993, 34, 2557.
83. Hudlicky, T.; Boros, C.H.; Boros, E.E. Tetrahedron: Asymmetry 1993, 4, 1365.
84. Kraus, A.G.; Gottschalk, P. J. Org. Chem. 1983, 48, 2111.