A three-component coupling approach to the marine bis-indole alkaloids: Topsentin, deoxytopsentin and bromotopsentin

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5503-5506

  Achab, Saïd ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BROMOTOPSENTIN; INDOLE ALKALOID; TOPSENTIN;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030605863     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01148-3     Document Type: Article

References (21)

1. 1. Kalinin, V. N. Synthesis 1992, 413-432. Martin, A. R., Yang, Y. Acta Chem. Scand. 1993, 47, 221-230.
2. 1. Kalinin, V. N. Synthesis 1992, 413-432. Martin, A. R., Yang, Y. Acta Chem. Scand. 1993, 47, 221-230.
3. 2. (a) Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1995, 36, 2615-2618.
4. (b) Choshi, T.; Yamada, S.; Sugino, E.; Kuwada, T.; Hibino, S. J. Org. Chem. 1995, 60, 5899-5904.
5. 3. (a) Bartik, K.; Braekman; J.-C., Daloze, D.; Stoller, C; Huysecom, J.; Vandevyver, G.; Ottinger, R. Can. J. Chem. 1987, 65, 2118-2121.
6. (b) Tsuji, S.; Rinehart, K. L.; Gunasekera, S. P.; Kashman, Y.; Cross, S. S.; Lui, M. S.; Pomponi, S. A.; Diaz, M. C. J. Org. Chem. 1988, 53, 5446-5453.
7. (c) Morris, S. A.; Andersen, R. J. Tetrahedron 1990, 46, 715-720.
8. 4. Braekman, J. C.; Daloze, D.; Stoller, C. Bull. Soc. Chim. Belg. 1987, 96, 809-812.
9. 5. Kaswasaki, I.; Yamashita, M.; Ohta, S. J. Chem. Soc., Chem. Commun. 1994, 2085-2086.
10. 6. James, P.; Snyder, H.R. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. 4, p. 539.
11. 2Cl) of the 6-benzyloxyindole prepared according to Moody, C.J. J. Chem. Soc., Perkin Trans 1 1984, 1333-1337.
12. 8. Saulnier, M.G.; Gribble, G.W. J. Org. Chem. 1983, 48, 2690-2695.
13. 9. Footnote 17 in ref. 2a. Also, see: Ciattini, P.G.; Morera, E.; Ortar, G. Tetrahedron lett. 1994, 35, 2405-2408.
14. 10. Groziak, M. P., Wei, L. J. Org. Chem. 1991, 56, 4296-4300.
15. 11. For a related example, see: Macor, J. E.; Ryan, K. Heterocyles 1994, 37, 1447-1450.
16. 12. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359-5364.
17. 13. Moyer, M.P.; Shiurba, J.F.; Rapoport, H. J. Org. Chem. 1986, 57, 5106-5110 and references cited.
18. 14. Bocchi, V.; Palla, G. Synthesis 1982, 1096-1097.
19. 10 as follows: protection (SEMCl, NaH, DMF) according to Whitten, J.P.; Matthews, D.P.; McCarthy, J.R. J. Org. Chem. 1986, 51, 1891-1894 and formylation (n-BuLi, DMF).
20. 16. For a related example of such a selectivity, see: Yang, Y.; Martin, A. R. Synth. Commun. 1992, 22, 1757-1762.
21. +.) 422.0185 found 422.0201.