The phenanthrenone approach to opium alkaloids: Formal total synthesis of morphine by sigmatropic rearrangement

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 441-444

  Mulzer, Johann ^a   Bats, Jan W ^b   List, Benjamin ^b   Opatz, Till ^b   Trauner, Dirk ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

^b GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002672380     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6135     Document Type: Article

References (30)

1. Mulzer, J.; Dümer, G.; Trauner, D. Angew. Chem. Int. Ed. Engl. 1996, 35, 2830
2. [Angew. Chem. 1996, 108, 3046].
3. For other recent syntheses of morphine alkaloids, see: a) Butora, G.; Hudlicky, T.; Fearnley, S.P.; Gum, A.G.; Stabile, M.R.; Abboud, K. Tetrahedron Lett. 1996, 37, 8155.
4. b) Parsons, P.J.; Penkett, C.S.; Shell, A. Chem. Rev. 1996, 96, 195.
5. c) Hong, C.Y.; Overman, L.E. Tetrahedron Lett. 1994, 35, 3453.
6. d) Hong, C.Y.; Kado, N.; Overman, L.E. J. Am. Chem. Soc. 1993, 115, 11028.
7. e) Parker, K.A.; Focas, D. J. Am. Chem. Soc. 1992, 114, 9688.
8. f) Tius, M.A.; Kerr, M.A. J. Am. Chem. Soc. 1992, 114, 5959.
9. For reviews of the total synthesis of morphine alkaloids, see: g) Hudlicky, T.; Butora, G.; Fearnley, S.P.; Gum, A.G.; Stabile, M.R. in Studies in Natural Products Chemistry (Ed.: Atta-ur-Rahman); Vol. 18, p. 43; Elsevier: Amsterdam 1996.
10. h) Maier, M. in Organic Synthesis Highlights II (Ed: Waldmann, H.); p. 357; VCH: Weinheim 1995.
11. j) Szántay, G.; Dörnyei, G. in The Alkaloids (Eds.: Cordell, G.A.; Brossi, A.); Vol. 45, p. 127; Academic Press: New York 1994.
12. For an excellent review of [3,3]-sigmatropic rearrangements, see: Frauenrath, H. in Houben-Weyl, Methoden der Organischen Chemie (Eds.: Helmchen, G.; Hoffmann, R.W.; Mulzer, J.; Schaumann, E.); Vol. E21d, p. 3301 ; Thieme: Stuttgart 1995.
13. a) Chida, N.; Sugihara, K.; Ogawa, S. J. Chem. Soc. Chem. Commun. 1994, 901.
14. b) Bauermeister S.; Gouws, I.D.; Strauss, H.F.; Venter, E.M.M. J. Chem. Soc. Chem. Perkin Trans. 1 1991, 561.
15. c) Fujioka, H.; Annoura, H.; Murano, K.; Kita, Y.; Tamura, Y. Chem. Pharm. Bull. 1989, 37(8), 2047.
16. d) Keck, G.E.; Webb II, R.R. J. Org. Chem. 1982, 47, 1303.
17. e) Srikrishna, A.; Krishnan, K. Tetrahedron 1992, 48, 3429.
18. Moss, W.H.; Gless, R.D.; Rapoport, H. J. Org. Chem. 1983, 48, 227.
19. a) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1956, 78, 1380.
20. b) Gates, M.; Tschudi, G. J. Am. Chem. Soc. 1953, 75, 379.
21. Wick, A.E.; Felix, D.; Steen. K.; Eschenmoser, A. Helv. Chim. Acta 1966, 47, 2425.
22. Details of the crystal structure determinations may be obtained from: The Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1 EZ, UK.
23. Still, W.C.; Mitra, A. J. Am. Chem. Soc. 1978, 100, 1927.
24. Tsunoda, T.; Yamamiya, Y.; Itô, S. Tetrahedron Lett. 1993, 34, 1639.
25. For a similar reaction, see: Labidalle, S.; Min, Z.Y.; Reynet, A.; Moskowitz, H.; Vierfond, J.-M.; Miocque, M. Tetrahedron 1988, 44, 1171.
26. 3): δ 143.59, 143.42, 137.40, 132.48, 132.26, 128.97, 127.17, 124.67, 123.20, 113.55, 96.30, 72.38, 56.42, 46.19, 46.06, 35.47, 34.47, 34.08, 29.41, 24.67, 23.12, 19.88.
27. Chan, T.H.; Brook, M.A.; Chaly, T. Synthesis 1983, 203.
28. Madsen, R.; Fraser-Reid, B. in Modem Methods in Carbohydrate Synthesis (Eds.: Khan, S.H.; O'Neill, R.A.); p. 155; Amsterdam: Harwood 1996.
29. Opatz, T. Diplomarbeit, Johann Wolfgang Goethe-Universität Frankfurt, 1997.
30. Porth, S. Diplomarbeit, Johann Wolfgang Goethe-Universität Frankfurt, 1997.