Indole-β-nucleophilic substitution. Part 91 nitrogen nucleophiles. Syntheses of hydroxycryptolepine, cryptolepine, and quindoline

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4283-4286

  Cooper, Melanie M ^a,b   Lovell, James M ^a   Joule, John A ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b CLEMSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CRYPTOLEPINE; HYDROXYCRYPTOLEPINE; INDOLE DERIVATIVE; QUINDOLINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; TRADITIONAL MEDICINE;

EID: 0029994789     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00818-0     Document Type: Article

References (26)

1. Part 8 to be ref 12(b); Part 7 and references therein: Dalton, L.; Humphrey, G. L.; Cooper, M. M.; Joule, J. A., J. Chem. Soc., Perkin Trans. 1, 1983, 2417.
2. Paulo, A.; Gomes, E. T.; Houghton, P. J., J. Nat. Prod., 1995, 58, 1485.
3. Cimanga, K.; De Bruyne, T.; Pieters, L.; Claeys, M.; Vlietinck, A.; Tetrahedron Lett., 1996, 37, 1703
4. Pousset, J.-L.; Martin, M.-T.; Jossang, A.; Bodo, B., Phytochemistry, 1995, 39, 735.
5. Tackie, A. N.; Boye, G. L.; Sharaf, M. H. M.; Schiff, P. L.; Crouch, R. C.; Spitzer, T. D.; Johnson, R. L.; Dunn, J.; Minick, D.; Martin, G. E., J. Nat. Prod., 1993, 56, 653.
6. Cimanga, K.; De Bruyne, T.; Lasure, A.; Van Poel, B.; Pieters, L.; Claeys, M.; Vanden Berghe, D.; Vlietinck, A., Planta Med., 1995, in press.
7. As cited in reference 3.
8. Gellért, E.; Raymond-Hamet; Schlittler, E., Helv. Chim. Acta, 1951, 34, 642.
9. Holt, S. J.; Petrow, V., J. Chem. Soc., 1947, 607 and references therein.
10. Dwuma-Badu, D.; Ayim, J. S. K.; Fiagbe, F. N. I. Y.; Knapp, J. E.; Schiff, P. L.; Slatkin, D. J., J. Pharm. Sci., 1978, 67, 433.
11. Sundberg, R. J.; Russell, H. F., J. Org. Chem., 1973, 38, 3324.
12. (a) Cooper, M. M.; Hignett, G. J.; Newton, R. F.; Joule, J. A.; Harris M.; Hinchley, J. D., J. Chem. Soc., Chem. Commun., 1977, 432; Cooper, M. M.; Hignett, G. J.; Joule, J. A., J. Chem. Soc., Perkin Trans. 1, 1981, 3008;
13. (a) Cooper, M. M.; Hignett, G. J.; Newton, R. F.; Joule, J. A.; Harris M.; Hinchley, J. D., J. Chem. Soc., Chem. Commun., 1977, 432; Cooper, M. M.; Hignett, G. J.; Joule, J. A., J. Chem. Soc., Perkin Trans. 1, 1981, 3008;
14. (b) Glendinning, A.; Hunter, W. N.; Joule, J. A.; Leonard, G. A., Acta Crystallogr., Sect. C, 1993, 49, 2126.
15. N-Methylphthalimidine did not react with 2-lithio-1-phenylsulfonylindole.
16. Graebe, C., Justus Liebigs Ann. Chem., 1888, 247, 288.
17. Tull, R.; O'Neill, R. C.; McCarthy, E. P.; Pappas, J. J.; Chernarda, J. M., J. Org. Chem., 1964, 29, 2425.
18. 3) except where otherwise specified.
19. 2).
20. 2).
21. 2).
22. H 9.5 (1H, bs, NH), 6.9 (1H, s, indole-3-H).
23. 6-DMSO) 12.2 (1H, bs, NH).
24. 6-DMSO) 12.95 (1H, bs, NH), 11.67 (1H, bs, NH).
25. 6-DMSO) (300 MHz) 12.0 (1H, bs), 8.56 (1H, d, J 7.9), 8.50 (1H, d, J 8.5), 8.03 (1H, d, J 8.8), 7.89 (1H, bt), 7.68 (1H, d, J 8.2), 7.59 (1H, bt), 7.47 (1H, bt), 7.31 (1H, bt).
26. We thank Dr. P. J. Houghton, Pharmacognosy Research Laboratories, Department of Pharmacy, King's College, London, for carrying out the direct tic comparison with the natural material.