Total synthesis of (-)-morphine

Chemistry - An Asian Journal

Volumn 5, Issue 10, 2010, Pages 2192-2198

  Koizumi, Hifumi ^a   Yokoshima, Satoshi ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Alkaloids; Crosscoupling; Enzyme catalysis; Michael addition; Total synthesis

Indexed keywords

ALKALOIDS; CROSS-COUPLINGS; ENZYME CATALYSIS; MICHAEL ADDITION; TOTAL SYNTHESIS;

ADDITION REACTIONS; CATALYSIS; CONDENSATION REACTIONS; ENZYMES; METABOLITES; NITROGEN COMPOUNDS;

SYNTHESIS (CHEMICAL);

ENZYME; MORPHINE;

ARTICLE; BIOCATALYSIS; CHEMISTRY; METABOLISM; STEREOISOMERISM; SYNTHESIS;

BIOCATALYSIS; ENZYMES; MORPHINE; STEREOISOMERISM;

EID: 77957564275     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000458     Document Type: Article

References (48)

1. M. Gate, G. Tschudi, J. Am. Chem. Soc. 1952, 74, 1109;
2. D. Ginsberg, D. Elad, J. Am. Chem. Soc. 1954, 76, 312;
3. R. Grewe, W. Friedrichsen, Chem. Ber. 1967, 100, 1550;
4. K. C. Rice, J. Org. Chem. 1980, 45, 3135;
5. D. A. Evans, C. H. Mitch, Tetrahedron Lett. 1982, 23, 285;
6. W. H. Moos, R. D. Gless, H. Rapoport, J. Org. Chem. 1983, 48, 227;
7. J. E. Toth, P. L. Fuchs, J. Org. Chem. 1986, 51, 2594;
8. J. E. Toth, P. R. Hamann, P. L. Fuchs, J. Org. Chem. 1988, 53, 4694;
9. M. A. Tius, M. A. Kerr, J. Am. Chem. Soc. 1992, 114, 5959;
10. K. A. Parker, D. Fokas, J. Am. Chem. Soc. 1992, 114, 9688;
11. C. Y. Hong, N. Kado, L. E. Overman, J. Am. Chem. Soc. 1993, 115, 11028;
12. J. D. White, P. Hrnciar, F. Stappenbeck, J. Org. Chem. 1997, 62, 5250;
13. D. Trauner, J. W. Bats, A. Werner, J. Mulzer, J. Org. Chem. 1998, 63, 5908;
14. G. Butora, T. Hudlicky, S. P. Fearnley, M. R. Stabile, A. G. Gum, D. Gonzales, Synthesis 1998, 665;
15. J.-P. Liou, C.-Y. Cheng, Tetrahedron Lett. 2000, 41, 915;
16. O. Yamada, K. Ogasawara, Org. Lett. 2000, 2, 2785;
17. H. Nagata, N. Miyazawa, K. Ogasawara, Chem. Commun. 2001, 1094;
18. D. F. Taber, T. D. Neubert, A. L. Rheingold, J. Am. Chem. Soc. 2002, 124, 12416;
19. B. M. Trost, W. Tang, J. Am. Chem. Soc. 2002, 124, 14542;
20. B. M. Trost, W. Tang, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 14785;
21. K. A. Parker, D. Fokas, J. Org. Chem. 2006, 71, 449;
22. K. Uchida, S. Yokoshima, T. Kan, T. Fukuyama, Org. Lett. 2006, 8, 5311;
23. A. T. Omori, K. J. Finn, H. Leisch, R. J. Carroll, T. Hudlický, Synlett 2007, 2859;
24. H. Tanimoto, R. Saito, N. Chida, Tetrahedron Lett. 2008, 49, 358;
25. M. Varin, E. Barré, B. Iorga, C. Guillou, Chem. Eur. J. 2008, 14, 6606;
26. K. Uchida, S. Yokoshima, T. Kan, T. Fukuyama, Heterocycles 2009, 77, 1219;
27. G. Stork, A. Yamashita, J. Adams, G. R. Schulte, R. Chesworth, Y. Miyazaki, J. J. Farmer, J. Am. Chem. Soc. 2009, 131, 11402;
28. P. Magnus, N. Sane, B. P. Fauber, V. Lynch, J. Am. Chem. Soc. 2009, 131, 16045;
29. H. Leisch, A. T. Omori, K. J. Finn, J. Gilmet, T. Bissett, D. Ilceski, T. Hudlický, Tetrahedron 2009, 65, 9862.
30. For a review on the synthesis of morphine, see: J. Zezula, T. Hudlický, Synlett 2005, 388.
31. For similar strategies using the Heck reaction in the synthesis of galanthamine, see: a) C. Pilger, B. Westermann, U. Flörke, G. Fels, Synlett 2000, 1163;
32. P. J. Parsons, M. D. Charles, D. M. Harvey, L. R. Sumoreeah, A. Shell, G. Spoors, A. L. Gell, S. Smith, Tetrahedron Lett. 2001, 42, 2209.
33. J. E. Yeo, X. Yang, H. J. Kim, S. Koo, Chem. Commun. 2004, 236.
34. For the enzymatic resolution of 6-acetoxycyclohex-2-enone, see: C. Tanyeli, E. Turkut, I. M. Akhmedov, Tetrahedron: Asymmetry 2004, 15, 1729.
35. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
36. A. Kamatani, L. E. Overman, J. Org. Chem. 1999, 64, 8743.
37. I. Hayakawa, M. Ueda, M. Yamaura, Y. Ikeda, Y. Suzuki, K. Yoshizato, H. Kigoshi, Org. Lett. 2008, 10, 1859.
38. K. M. Markovich, V. Tantishaiyakul, A. Hamada, D. D. Miller, K. J. Romstedt, G. Shams, Y. Shin, P. F. Fraundorfer, K. Doyle, D. R. Feller, J. Med. Chem. 1992, 35, 466.
39. O. Mitsunobu, M. Yamada, Bull. Chem. Soc. Jpn. 1967, 40, 2380;
40. O. Mitsunobu, Synthesis 1981, 1.
41. For a review on the intramolecular Heck reaction, see: J. T. Link, Org. React. 2002, 60, 157.
42. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155.
43. T. Fukuyama, M. Cheung, C.-K. Jow, Y. Hidai, T. Kan, Tetrahedron Lett. 1997, 38, 5831;
44. T. Kan, T. Fukuyama, J. Synth. Org. Chem. Jpn. 2001, 59, 779;
45. T. Kan, T. Fukuyama, Chem. Commun. 2004, 353.
46. During this transformation, partial elimination of the β-mesyloxy group afforded a conjugated dienone in 17% yield, which could also be converted into a mixture of neopinone and codeinone by cleavage of the DNs group under the same conditions. For details, see the Supporting Information.
47. K. C. Rice, J. Med. Chem. 1977, 20, 164.
48. N. E. Schore, M. J. Knudsen, J. Org. Chem. 1987, 52, 569.