Reactivity of hexahydrocarbazol-4-ones in Michael reactions: Stereocontrolled formation of decahydropyrido[2,3-d]carbazoles

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 14, 1998, Pages 2145-2149

  Dugat, Denise ^a   Benchekroun Mounir, Nora ^a   Dauphin, Gérard ^a   Gramain, Jean Claude ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748725044     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a802620c     Document Type: Article

References (21)

1. A. Brossi and M. Suffness, in The Alkaloids, Antitumor Bisindole Alkaloids from Catharanthus Roseus, Academic Press, San Diego, 1990, vol. 37;
2. P. L. Feldman and H. Rapoport, J. Am. Chem. Soc., 1987, 109, 1603 and references cited therein;
3. P. Magnus, M. Ladlow and J. Elliot, J. Am. Chem. Soc., 1987, 109, 7929;
4. J. D. Phillipson and M. H. Zenk, in Indole and Biogenetically Related Alkaloids, Academic Press, New York, 1980.
5. (a) J.-C. Gramain, Y. Troin and H.-P. Husson, J. Heterocycl. Chem., 1988, 25, 201;
6. (b) D. Dugat, J.-C. Gramain and G. Dauphin, J. Chem. Soc., Perkin Trans. 2, 1990, 605.
7. (a) N. Benchekroun-Mounir, D. Dugat and J.-C. Gramain, Tetrahedron Lett., 1992, 33, 4001;
8. (b) N. Benchekroun-Mounir, D. Dugat, J.-C. Gramain and H.-P. Husson, J. Org. Chem., 1993, 58, 6457.
9. (a) J.-C. Gramain, H.-P. Husson and Y. Troin, J. Org. Chem., 1985, 50, 5517;
10. (b) D. Gardette, J.-C. Gramain and M.-E. Sinibaldi, Heterocycles, 1990, 31, 1439;
11. (c) M. Dufour, J.-C. Gramain, H.-P. Husson, M.-E. Sinibaldi and Y. Troin, J. Org. Chem., 1990, 55, 5483.
12. L. E. Overman and S. R. Angle, J. Org. Chem., 1985, 50, 4021.
13. For preparation see: E. C. Du Feu, F. J. McQuillin and R. Robinson, J. Chem. Soc., 1937, 53.
14. F. F. Blicke, Org. React., 1965, 303.
15. 13C NMR Spectroscopy, Academic Press, New York, 1972, vol. 24, (a) pp. 412 and 413;
16. 13C NMR Spectroscopy, p. 65;
17. 13C NMR Spectroscopy, p. 288.
18. M. Hudlicky, in Reductions in Organic Chemistry, Wiley, New York, 1984, p. 135;
19. E. M. Hancock and A. C. Cope, Org. Synth., 1955, 501.
20. E. Eliel and S. H. Wilen, in Stereochemistry of Organic Compounds, Wiley, New York, 1994, pp. 774-780;
21. M. Hanack, in Conformation Theory, Academic Press, New York, 1965, pp. 176 and 200.