Preparation of pilot library with tetrahydro-β-carboline alkaloid core skeleton using tandem intramolecular Pictet-Spengler cyclization

Tetrahedron Letters

Volumn 47, Issue 38, 2006, Pages 6843-6847

  Lee, Sung Chan ^a   Choi, Soo Young ^a   Chung, Young Keun ^a   Park, Seung Bum ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHOXY 4 ALKOXYBENZYL ALCOHOL; ALCOHOL DERIVATIVE; ALKALOID DERIVATIVE; TRYPTOLINE DERIVATIVE; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; PICTET SPENGLER REACTION; SOLID;

EID: 33747187760     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.051     Document Type: Article

References (31)

1. Ho B.T., McIsaak W.M., Walker K.E., and Estevez V. J. Pharm. Sci. 57 (1968) 269
2. Airaksinen M.M., and Kari I. Med. Biol. 59 (1981) 21
3. Leteurtre F., Sackett D.L., Madalengoitia J., Kohlhagan G., Macdonald T.L., Hamel E., Paul K.D., and Pommier Y. Biochem. Pharmacol. 19 (1995) 128
4. Sunder-Plassmann N., Sarli V., Gartner M., Utz M., Seiler J., Huemmer S., Mayer T.U., Surrey T., and Giannis A. Bioorg. Med. Chem. 13 (2005) 6094
5. Trudell M.L., Soerens D., Weber R.W., Hutchins L., Grubisha D., Bennett D., and Cook J.M. Tetrahedron 48 (1992) 1805
6. Danieli B., Giovanelli P., Lesma G., Passarella D., Sacchetti A., and Silvani A. J. Comb. Chem. 7 (2005) 458
7. Castro A.C., Dang L.C., Soucy F., Grenier L., Mazdiyasni H., Hottelet M., Parent L., Pien C., Palombella V., and Adams J. Bioorg. Med. Chem. Lett. 13 (2003) 2419
8. Maw G.N., Allerton C.M.N., Gbekor E., and Million W.A. Bioorg. Med. Chem. Lett. 13 (2003) 1425
9. Farzin D., and Mansouri N. Eur. Neuropsychopharm. 16 (2006) 324
10. Kusurkar R.S., and Goswami S.K. Tetrahedron 60 (2004) 5315
11. Kuo F.M., Tseng M.-C., Yen Y.-H., and Chu Y.-H. Tetrahedron 60 (2004) 12075
12. Ardeo A., García E., Arrasate S., Lete E., and Sotomayor N. Tetrahedron Lett. 44 (2003) 8445
13. Santos L.S., Fernandes S.A., Pilli R.A., and Marsaioli A.J. Tetrahedron: Asymmetry 14 (2003) 2515
14. Tsuji R., Nakagawa M., and Nishida A. Tetrahedron: Asymmetry 14 (2003) 177
15. Jiang W., Sui Z., and Chen X. Tetrahedron Lett. 43 (2002) 8941
16. Paulvannan K., Hale R., Mesis R., and Chen T. Tetrahedron Lett. 43 (2002) 203
17. Mayer J.P., Bankaitis-Davis D., Zhang J., Beaton G., Bjergarde K., Andersen C.M., Goodman B.A., and Herrera C.J. Tetrahedron Lett. 37 (1996) 5633
18. Yang L., and Guo L. Tetrahedron Lett. 37 (1996) 5041
19. Fantauzzi P.P., and Yanger K.M. Tetrahedron Lett. 39 (1998) 1291
20. van Loevezijn A., van Maarseveen J.H., Stegman K., Visser G.M., and Koomen G.-J. Tetrahedron Lett. 39 (1998) 4737
21. Li X., Zhang L., Zhang W., Hall S.E., and Tam J.P. Org. Lett. 2 (2000) 3075
22. Bailey P.D., Collier I.D., and Hollinshead S.P. J. Chem. Soc., Perkin Trans. 8 (1997) 1209
23. Li J., and Cook J.M. J. Org. Chem. 63 (1998) 4166
24. Dai W., Zhu H., and Hao X. Tetrahedron Lett. 37 (1996) 5971
25. Cox E.D., Hamaker L.K., Li J., Yu P., Czerwinski K.M., Deng L., Bennett D.W., and Cook J.M. J. Org. Chem. 62 (1997) 44
26. Czarnocki Z., Mieczkowski J.M., Kiegiel J., and Araźny Z. Tetrahedron: Asymmetry 6 (1995) 2899
27. Ezquerra J., Lamas C., Pastor A., Alvarez P., Vaquero J.J., and Prowse W.G. Tetrahedron Lett. 37 (1996) 5813
28. Kawate T., Yamada H., Matsumizu M., Nishida A., and Nakagawa M. Synlett 7 (1997) 761
29. Lee S.-C., and Park S.B. J. Comb. Chem. 8 (2006) 50
30. w = 0.0833 (I > 2σ(I)). CCDC reference numbers 611436.
31. 1H, COSY, HSQC) and Mass Spectroscopy, but we failed to confirm the definitive stereochemistry of R diastereomer, because it was not crystallized for X-ray crystallographic study.