Total synthesis of (±)-morphine

Heterocycles

Volumn 77, Issue 2, 2009, Pages 1219-1234

  Uchida, Kenji ^a,b   Yokoshima, Satoshi ^a   Kan, Toshiyuki ^a,c   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYOWA HAKKO KOGYO CO LTD   (Japan)

^c UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Intramolecular Aldol Condensation; Intramolecular Mannich Type Reaction; Morphinan Skeleton; Morphine; Tandem Cyclization

Indexed keywords

EID: 68949141532     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(F)103     Document Type: Article

References (27)

1. M. Varin, E. Barr, B. Iorga, and C. Guillou Chem. Eur. J. 14 2008 6606
2. H. Tanimoto, R. Saito, and N. Chida Tetrahedron Lett. 49 2008 358
3. A.T. Omori, K.J. Finn, H. Leisch, R.J. Carroll, and T. Hudlicky Synlett 2007 2859
4. K. Uchida, S. Yokoshima, T. Kan, and T. Fukuyama Org. Lett. 8 2006 5311
5. K.A. Parker, and D. Fokas J. Org. Chem. 71 2006 449
6. B.M. Trost, W. Tang, and F.D. Toste J. Am. Chem. Soc. 127 2005 14785
7. B.M. Trost, and W. Tang J. Am. Chem. Soc. 124 2002 14542
8. D.F. Taber, T.D. Neubert, and A.L. Rheingold J. Am. Chem. Soc. 124 2002 12416
9. C.Y. Hong, N. Kado, and L.E. Overman J. Am. Chem. Soc. 115 1993 11028
10. For a review and other syntheses, see: J. Zezula, and T. Hudlicky Synlett 2005 388
11. Similar strategies using the Heck reaction have been employed to synthesize galanthamine:
12. C. Pilger, B. Westermann, U. Flrke, and G. Fels Synlett 2000 1163
13. P.J. Parsons, M.D. Charles, D.M. Harvey, L.R. Sumoreeah, A. Shell, G. Spoors, A.L. Gell, and S. Smith Tetrahedron Lett. 42 2001 2209
14. Y. Kaburagi, H. Tokuyama, and T. Fukuyama J. Am. Chem. Soc. 126 2004 10246 Although our procedure can yield optically pure epoxide in large quantities, the racemate was used in this preliminary study.
15. J. Tsuji, H. Kataoka, and Y. Kobayashi Tetrahedron Lett. 22 1981 2575
16. B.M. Trost, and G.A. Molander J. Am. Chem. Soc. 103 1981 5969
17. B.M. Trost, and R.W. Warner J. Am. Chem. Soc. 105 1983 5940
18. J. Tsuji Review: Palladium Reagents and Catalysts 1995 Wiley New York
19. H.P. Plaumann, B.A. Kaey, and R. Rodrigo Tetrahedron Lett. 20 1979 4921
20. O. Mitsunobu, and M. Yamada Bull. Chem. Soc. Jpn. 40 1967 2380
21. O. Mitsunobu Synthesis 1981 1
22. B.K. Wilk Synth. Commun. 23 1993 2481
23. Y. Itoh, T. Hirano, and T. Saegusa J. Org. Chem. 43 1978 1011
24. P.S. Wharton, and D.H. Bohlen J. Org. Chem. 26 1961 3615
25. P.S. Wharton J. Org. Chem. 26 1961 4781
26. D.H.R. Barton, R.S.H. Motherwell, and W.B. Motherwell J. Chem. Soc., Perkin Trans. 1 1981 2363
27. K.C. Rice J. Med. Chem. 20 1977 164