Stereoselective synthesis of thienyl and furyl analogues of ephedrine

Tetrahedron Asymmetry

Volumn 8, Issue 3, 1997, Pages 469-476

  Effenberger, Franz ^a   Eichhorn, Joachim ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EPHEDRINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HYDROGENATION; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031041041     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00528-9     Document Type: Article

References (33)

1. Enzyme Catalyzed Reactions, Part 27. Part 26: Effenberger, F.; Gutterer, B.; Jäger, J. Tetrahedron: Asymmetry 1997, 8, 459-467.
2. a) Engel, J. Chem.-Ztg. 1982, 106, 169-183.
3. b) Kleemann, A.; Engel, J. Pharmazeutische Wirkstoffe, Synthesen, Patente, Anwendungen; 2nd ed.; Thieme Verlag, Stuttgart, 1982, and supplementary volume 1987.
4. Engel, J. Chem.-Ztg. 1979, 103, 161-172.
5. Kanao, S. J. Pharm. Soc. Japan 1927, 550, 1019-1035; Chem. Abstr. 1928, 22, 1588.
6. Kanao, S. J. Pharm. Soc. Japan 1927, 550, 1019-1035; Chem. Abstr. 1928, 22, 1588.
7. Seelkopf, C. Rev. Fac. Farm., Univ. Los Andes (Venezuela), 1974, 75, 157-185; Chem. Abstr. 1975, 83, 78998q.
8. Seelkopf, C. Rev. Fac. Farm., Univ. Los Andes (Venezuela), 1974, 75, 157-185; Chem. Abstr. 1975, 83, 78998q.
9. a) Barker, J. M.; Byron, D. J.; Huddleston, P. R. J. Chem. Soc. (C) 1969, 2183-2185.
10. b) Barker, J. M.; Huddleston, P. R. J. Chem. Soc., Perkin Trans 1 1973, 1200-1203.
11. Mavrova, A.; Zhelyazkov, L. Farmatsiya (Sofia) 1986, 36, 1-5; Chem. Abstr. 1988, 108, 130714v.
12. Mavrova, A.; Zhelyazkov, L. Farmatsiya (Sofia) 1986, 36, 1-5; Chem. Abstr. 1988, 108, 130714v.
13. a) Effenberger, F. Angew. Chem. Int. Ed. Engl. 1994, 33, 1555-1564.
14. b) Ziegler, T.; Hörsch, B.; Effenberger, F. Synthesis 1990, 575-578.
15. c) Effenberger, F.; Ziegler, T.; Förster, S. Angew. Chem. Int. Ed. Engl. 1987, 26, 458-460.
16. d) Niedermeyer, U.; Kula, M.-R. Angew. Chem. Int. Ed. Engl. 1990, 29, 386-387.
17. e) Niedermeyer, U.; Kragl, U.; Kula, M.-R.; Wandrey, C.; Makryaleas, K.; Drauz, K.-H. (Kernforschungsanlage Jülich GmbH; Degussa AG), Eur. Pat. Appl. EP 326,063 A2, 1989; Chem. Abstr. 1990, 112, 234012p .
18. e) Niedermeyer, U.; Kragl, U.; Kula, M.-R.; Wandrey, C.; Makryaleas, K.; Drauz, K.-H. (Kernforschungsanlage Jülich GmbH; Degussa AG), Eur. Pat. Appl. EP 326,063 A2, 1989; Chem. Abstr. 1990, 112, 234012p .
19. f) Niedermeyer, U. Dissertation, Universität Düsseldorf, 1989.
20. a) Kruse, C. G. In Chirality in Industry; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley, New York, 1992, pp. 279-299.
21. b) Jackson, W. R.; Jacobs, H. A.; Jayatilake, G. S.; Matthews, B. R.; Watson, K. G. Aust. J. Chem. 1990, 43, 2045-2062.
22. a) Brussee, J.; Dofferhoff, F.; Kruse, C. G.; van der Gen, A. Tetrahedron 1990, 46, 1653-1658.
23. b) Effenberger, F.; Gutterer, B.; Ziegler, T. Liebigs Ann. Chem. 1991, 269-273.
24. Wessely, F.; Swoboda, W. Monatsh. Chem. 1951, 82, 621-627.
25. Effenberger, F.; Eichhorn, J.; Roos, J. Tetrahedron: Asymmetry 1995, 6, 271-282.
26. 8,9.
27. 8,9.
28. a) Hochuli, E. Helv. Chim. Acta 1983, 66, 489-493.
29. b) Kaul, R.; Mattiasson, B. Biotechnol. Appl. Biochem. 1987, 9, 294-302.
30. c) Lauble, H.; Müller, K.; Schindelin, H.; Förster, S.; Effenberger, F. Proteins: Struct, Funct., Genet. 1994, 19, 343-347.
31. a) Bové, C.; Conn, E. E. J. Biol. Chem. 1961, 236, 207-210.
32. b) Seely, M. K.; Criddle, R. S.; Conn, E. E. J. Biol. Chem. 1966, 241, 4457-4462.
33. c) Smitskamp-Wilms, E.; Brussee, J.; van der Gen, A.; van Scharrenburg, G. J. M.; Sloothaak, J. B. Recl. Trav. Chim. Pays-Bas 1991, 110, 209-215.