Practical ex-chiral-pool methodology for the synthesis of dopaminergic tetrahydroindoles

Tetrahedron

Volumn 60, Issue 5, 2004, Pages 1197-1204

  Bergauer, Markus ^a   Hübner, Harald ^a   Gmeiner, Peter ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Aminobutyrolactone; Asparagine; Ex chiral pool synthesis; Receptor binding

Indexed keywords

3 AMINOBUTYROLACTONE; 5 AMINOTETRAHYDROINDOLIZINE; 5 DIPROPYLAMINO 4,5,6,7 TETRAHYDROINDOLE; 6 AMINOTETRAHYDROINDOLIZINE; ASPARAGINE; DOPAMINE; DOPAMINE 3 RECEPTOR STIMULATING AGENT; INDOLE DERIVATIVE; LACTONE DERIVATIVE; NEUROTRANSMITTER; PYRROLE DERIVATIVE; TETRAHYDROINDOLE; UNCLASSIFIED DRUG;

ARTICLE; CHIRAL CHROMATOGRAPHY; EXPERIMENT; METHODOLOGY; PRIORITY JOURNAL; RECEPTOR BINDING; RECEPTOR BLOCKING; SYNTHESIS;

EID: 0346969563     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.041     Document Type: Article

References (31)

1. Coppola G.M., Schuster H.F. Asymmetric synthesis. 1987;Wiley, New York.
2. Gmeiner P. Juaristi E. Enantioselective synthesis of β-amino acids. 1997;67-81 Wiley-VCH, New York.
3. Gmeiner P., Feldman P.L., Chu-Moyer M.Y., Rapoport H. J. Org. Chem. 55:1990;3068.
4. Gmeiner P., Kärtner A., Junge D. Tetrahedron Lett. 34:1993;4325.
5. Gmeiner P., Kärtner A. Synthesis. 1995;83.
6. Weber K., Kuklinkski S., Gmeiner P. Org. Lett. 2:2000;647.
7. Weber K., Ohnmacht U., Gmeiner P. J. Org. Chem. 65:2000;7406.
8. Gmeiner P., Junge D., Kärtner A. J. Org. Chem. 59:1994;6766.
9. Gmeiner P., Mierau J., Höfner G. Arch. Pharm. (Weinheim). 325:1992;57.
10. Lehmann T., Hübner H., Gmeiner P. Bioorg. Med. Chem. Lett. 11:2001;2863.
11. Lehmann T., Gmeiner P. Heterocycles. 53:2000;1371.
12. Michel D., Waibel R., Gmeiner P. Heterocycles. 51:1999;365.
13. Andersen K.E., Braestrup C., Groenwald F.C., Joergensen A.S., Nielsen E.B., Sonnewald U., Soerensen P.O., Suzdak P.D., Knutsen L.J.S. J. Med. Chem. 36:1993;1716.
14. Harrowven D.C., Dainty R.F. Tetrahedron Lett. 36:1995;6739.
15. Lau C.K., Tardif S., Dufresne C., Scheigetz J. J. Org. Chem. 54:1989;491.
16. Baldwin J.E. J. Chem. Soc., Chem. Commun. 18:1976;734.
17. Perri S.T., Foland L.D., Decker O.H.W., Moore H.W. J. Org. Chem. 51:1986;3065.
18. Hasan I., Marinelli E.R., Lin L.-C.C., Fowler F.W., Levy A.B. J. Org. Chem. 46:1981;157.
19. Edwards M.P., Doherty A.M., Ley S.V., Organ H.M. Tetrahedron. 42:1986;3723.
20. Martinez G.R., Grieco P.A., Srinivasan C.V. J. Org. Chem. 46:1981;3760.
21. Nicolaou K.C., Papahatjis D.P., Claremon D.A., Magolda R.L., Dolle R.E. J. Org. Chem. 50:1985;1440.
22. Hobbs C.F., McMillin C.K., Papadopoulus E.P., Vander Werf C.A. J. Am. Chem. Soc. 84:1962;43.
23. Bray B.L., Mathies P.H., Naef R., Solas D.R., Tidwell T.T., Artis D.R., Muchowski J.M. J. Org. Chem. 55:1990;6317.
24. Bach N.J., Kornfeld E.D., Jones N.D., Chaney M.O., Dorman D.E., Paschal J.W., Clemens J.A., Smalstig E.B. J. Med. Chem. 23:1980;481.
25. Bosch J., Roca T., Perez C.G., Montanari S. Bioorg. Med. Chem. Lett. 10:2000;563.
26. Hayes G., Biden T.J., Selbie L.A., Shine J. Mol. Endocrinol. 6:1992;920.
27. Sokoloff P., Andrieux M., Besançon R., Pilon C., Martres M.-P., Giros B., Schwartz J.-C. Eur. J. Pharmacol. 225:1992;331.
28. Asghari V., Sanyal S., Buchwaldt S., Paterson A., Jovanovic V., Van Tol H.H.M. J. Neurochem. 65:1995;1157.
29. Hübner H., Haubmann C., Utz W., Gmeiner P. J. Med. Chem. 43:2000;756.
30. Cheng Y.C., Prusoff W.H. Biochem. Pharmacol. 22:1973;3099.
31. Hübner H., Kraxner J., Gmeiner P. J. Med. Chem. 43:2000;4563.