Synthesis of chiral and achiral analogues of ambroxol via palladium-catalysed reactions

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 19, 1997, Pages 2873-2877

  Larsson, Anna L E ^a   Gatti, Roberto G P ^a   Bäckvall, Jan E ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748625484     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702141k     Document Type: Article

References (24)

1. (a) H. Koch, Drugs Today, 1979, 15, 523;
2. (b) G. Caramia, R. Gagliardini, E. Ruffini, P. Osimani and A. Nobilini, J. Int. Med. Res., 1995, 23, 284;
3. (c) W. Kuckelt, R. Dauberschmidt, J. Scharfenberg, K. Winsel, B. Lachmann, H. Frenzke, U. Hieronymi, H. Mrochen and M. Meyer, Respiration, 1980, 39, 264.
4. M. Bianchi, A. Mantovani, A. Erroi, C. A. Dinarello and P. Ghezzi, Agents Actions 1990, 31, 275 and references cited therein.
5. In cooperation with: T. Eriksson, C. M. Andersson, H. Bergstrand, K. Karabelas and P. Sjö at the Department of Medicinal Chemistry, Astra Draco AB, PO Box 34, S-221 00 Lund, Sweden.
6. (a) K. Ramesh, M. S. Wolfe, Y. Lee, D. Vander Velde and R. T. Borchardt, J. Org. Chem., 1992, 57, 5861;
7. (b) N. Dyatkina, B. Costisella, F. Theil and M. von Janta-Lipinski, Tetrahedron Lett., 1994, 35, 1961;
8. (c) N. B. Dyatkina, F. Theil and M. von Janta-Lipinski, Tetrahedron, 1995, 51, 761.
9. (a) S. Knapp, A. B. J. Naughton and T. G. Murali Dhar, Tetrahedron Lett., 1992, 33, 1025;
10. (b) T. Hudlicky and H. F. Olivo, Tetrahedron Lett., 1991, 32, 6077.
11. R. G. P. Gatti, A. L. E. Larsson and J. E. Bäckvall, J. Chem. Soc., Perkin Trans. 1, 1997, 577.
12. For related work on enantioselective synthesis of 4-aminocyclohex-2-enols see: B. M. Trost and S. R. Pulley, J. Am. Chem. Soc., 1995, 117, 10 143;
13. B. M. Trost, Pure Appl. Chem., 1996, 68, 779.
14. J. E. Bäckvall, R. Gatti and H. E. Schink, Synthesis, 1993, 343.
15. R. J. Kazlauskas, A. N. E. Weissfloch, A. T. Rappaport and L. A. Cuccia, J. Org. Chem., 1991, 56, 2656.
16. J. E. Bäckvall, S. E. Byström and S. E. Nordberg, J. Org. Chem., 1984, 49, 4619.
17. (a) J. E. Bäckvall, J. E. Nyström and S. E. Nordberg, J. Am. Chem. Soc., 1985, 107, 3676;
18. (b) J. Vågberg and J. E. Bäckvall, Org. Synth., 1990, 69, 38.
19. (a) J. E. Bäckvall, in Advances in Metal-Organic Chemistry, ed. L. S. Liebeskind, JAI press, Greenwich, CT, 1989, vol. 1, pp. 135-175;
20. (b) J. E. Bäckvall, Palladium-Catalyzed 1,4-Additions to Conjugated Dienes, a review in 'Metal-catalyzed Cross Coupling Reactions', ed. P. Stang and F. Diederich, VCH, Weinham, in the press;
21. (c) P. G. Andersson and J. E. Bäckvall, in Advances in Natural Product Synthesis, ed. W. Pearson, JAI Press, 1996;
22. (d) H. E. Schink, H. Pettersson and J. E. Bäckvall, J. Org. Chem., 1991, 56, 2769;
23. (e) D. Tanner, M. Sellén and J. E. Bäckvall, J. Org. Chem., 1989, 54, 3374.
24. T. Ukai, H. Kawazura, Y. Ishii, J. J. Bonnet and J. A. Ibers, Organomet. Chem., 1974, 65, 253.