Liquid-phase parallel synthesis of tetrahydro-β-carbolines

Tetrahedron Letters

Volumn 44, Issue 26, 2003, Pages 4923-4926

  Yeh, Wen Ben ^a   Lin, Mei Jung ^a   Sun, Chung Ming ^a  

^a NATIONAL DONG HWA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; BETA CARBOLINE DERIVATIVE; KETONE DERIVATIVE; MACROGOL; POLYMER; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; MASS SPECTROMETRY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037534860     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01100-6     Document Type: Article

References (30)

1. Thompson L.A., Ellman J.A. Chem. Rev. 96:1996;555.
2. Dolle R.E. J. Comb. Chem. 2:2000;383.
3. Hermkens P.H.H., Plate R., Kruse C.G., Scheeren H.W., Ottenheijm H.C.J. J. Org. Chem. 57:1992;3881.
4. Chi D.Y., O'Neil J.P., Anderson C.J., Welch M.J., Katzenellenbogen J.A. J. Med. Chem. 37:1994;928.
5. Leteurtre F., Sackett D.L., Madalengoitia J., Kohlhagan G., Macdonald T.L., Hamel E., Paul K.D., Pommier Y. Biochem. Pharmacol. 19:1995;128.
6. Ho B.T. J. Pharm. Sci. 61:1972;821.
7. Wang H., Ganesan A. Org. Lett. 1:1999;1647.
8. Cui C.B., Kakeya H., Osada A. Tetrahedron. 53:1997;59.
9. Usui T., Kondoh M., Cui C.B., Mayumi T., Osada H. Biochem. J. 333:1998;543-548.
10. Kondoh M., Usui T., Mayumi T., Osada H. J. Antibiot. 51:1998;801.
11. Liu X., Deschamp J.R., Cook J.M. Org. Lett. 4:2002;3339.
12. Cain M., Weber R.W., Guzman F., Cook J.M., Barker S.A., Rice K.C., Crawley J.N., Paul S.M., Skolnick P. J. Med. Chem. 25:1982;1081.
13. For a review, see: Sun C.M. Comb. Chem. High Throughput Screening. 2:1999;299 For a book chapter, see: Sun, C. M. In Combinatorial Chemistry Methods and Protocols, Methods in Molecular Biology Series; Bellavance, L., Ed.; Soluble Polymer-Supported Synthesis of Heterocyclic Libraries. Humana Press: New Jersey, 2002; Chapter 10, pp. 345-371.
14. Annunziata R., Benaglia M., Cinquini M., Cozzi F. Chem. Eur. J. 6:2000;133.
15. Reggelin M., Brenig V., Zur C. Org. Lett. 2:2000;531.
16. Pan P.C., Sun C.M. Tetrahedron Lett. 39:1998;9505.
17. Shey J.Y., Sun C.M. Synlett. 12:1998;1423.
18. Shey J.Y., Sun C.M. J. Comb. Chem. 1:1999;361.
19. Yeh C.M., Tung C.L., Sun C.M. J. Comb. Chem. 2:2000;341.
20. Bendale P.M., Sun C.M. J. Comb. Chem. 4:2002;359.
21. Shey J.Y., Sun C.M. Tetrahedron Lett. 43:2002;1725.
22. Wu C.Y., Sun C.M. Synlett. 10:2002;1709.
23. Sun C.M., Swamy K.M.K., Lin M.J., Yeh W.B., Chen F.Y., Tseng W.H. Comb. Chem. High Throughput Screening. 6:2003;123.
24. For solid-phase Pictet-Spengler reaction, see: (a) Mayer, J. P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C. M.; Goodman, B. A.; Herrera, C. J. Tetrahedron Lett. 1996, 37, 5633; (b) Yang, L.; Guo, L. Tetrahedron Lett. 1996, 37, 5041; (c) Fantauzzi, P. P.; Yanger, K. M. Tetrahedron Lett. 1998, 39, 1291; (d) van Loevezijn, A.; van Maarseveen, J. H.; Stegman, K.; Visser, G. M.; Koomen, G.-J. Tetrahedron Lett. 1998, 39, 4737; (e) Li, X.; Zhang, L.; Zhang, W.; Hall, S. E.; Tam, J. P. Org. Lett. 2000, 2, 3075.
25. For solid-phase Pictet-Spengler reaction, see: (a) Mayer, J. P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C. M.; Goodman, B. A.; Herrera, C. J. Tetrahedron Lett. 1996, 37, 5633; (b) Yang, L.; Guo, L. Tetrahedron Lett. 1996, 37, 5041; (c) Fantauzzi, P. P.; Yanger, K. M. Tetrahedron Lett. 1998, 39, 1291; (d) van Loevezijn, A.; van Maarseveen, J. H.; Stegman, K.; Visser, G. M.; Koomen, G.-J. Tetrahedron Lett. 1998, 39, 4737; (e) Li, X.; Zhang, L.; Zhang, W.; Hall, S. E.; Tam, J. P. Org. Lett. 2000, 2, 3075.
26. For solid-phase Pictet-Spengler reaction, see: (a) Mayer, J. P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C. M.; Goodman, B. A.; Herrera, C. J. Tetrahedron Lett. 1996, 37, 5633; (b) Yang, L.; Guo, L. Tetrahedron Lett. 1996, 37, 5041; (c) Fantauzzi, P. P.; Yanger, K. M. Tetrahedron Lett. 1998, 39, 1291; (d) van Loevezijn, A.; van Maarseveen, J. H.; Stegman, K.; Visser, G. M.; Koomen, G.-J. Tetrahedron Lett. 1998, 39, 4737; (e) Li, X.; Zhang, L.; Zhang, W.; Hall, S. E.; Tam, J. P. Org. Lett. 2000, 2, 3075.
27. For solid-phase Pictet-Spengler reaction, see: (a) Mayer, J. P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C. M.; Goodman, B. A.; Herrera, C. J. Tetrahedron Lett. 1996, 37, 5633; (b) Yang, L.; Guo, L. Tetrahedron Lett. 1996, 37, 5041; (c) Fantauzzi, P. P.; Yanger, K. M. Tetrahedron Lett. 1998, 39, 1291; (d) van Loevezijn, A.; van Maarseveen, J. H.; Stegman, K.; Visser, G. M.; Koomen, G.-J. Tetrahedron Lett. 1998, 39, 4737; (e) Li, X.; Zhang, L.; Zhang, W.; Hall, S. E.; Tam, J. P. Org. Lett. 2000, 2, 3075.
28. For solid-phase Pictet-Spengler reaction, see: (a) Mayer, J. P.; Bankaitis-Davis, D.; Zhang, J.; Beaton, G.; Bjergarde, K.; Andersen, C. M.; Goodman, B. A.; Herrera, C. J. Tetrahedron Lett. 1996, 37, 5633; (b) Yang, L.; Guo, L. Tetrahedron Lett. 1996, 37, 5041; (c) Fantauzzi, P. P.; Yanger, K. M. Tetrahedron Lett. 1998, 39, 1291; (d) van Loevezijn, A.; van Maarseveen, J. H.; Stegman, K.; Visser, G. M.; Koomen, G.-J. Tetrahedron Lett. 1998, 39, 4737; (e) Li, X.; Zhang, L.; Zhang, W.; Hall, S. E.; Tam, J. P. Org. Lett. 2000, 2, 3075.
29. Ungemach F., Sorens D., Weber R., Dipierro M., Campos O., Mokry P., Cook J.M., Silverton J.V. J. Am. Chem. Soc. 102:1980;6976.
30. 2S: m/z 390.0037. Found 390.0022.