Total synthesis of (-)-normalindine via addition of metalated 4-methyl-3-cyanopyridine to an enantiopure sulfinimine

Journal of Organic Chemistry

Volumn 71, Issue 23, 2006, Pages 8761-8766

  Davis, Franklin A ^a   Melamed, Jeffrey Y ^a   Sharik, Steven S ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ISOMERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ENANTIOPURE SULFINIMINE; NORMALINDINE;

NITROGEN COMPOUNDS;

4 METHYL 3 CYANOPYRIDINE; ALKALOID; IMINE; NAPHTHYRIDINE DERIVATIVE; NORMALINDINE; PYRIDINE DERIVATIVE; SULFINIMINE; SULFUR DERIVATIVE; TETRAHYDRONAPHTHYRIDINE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; METALLATION; REACTION ANALYSIS; SYNTHESIS;

IMINES; MOLECULAR CONFORMATION; NAPHTHYRIDINES; NITRILES; PYRIDINES; STEREOISOMERISM; SULFONIUM COMPOUNDS;

EID: 33750893707     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061443+     Document Type: Article

References (32)

1. (a) Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 30, p 252.
2. (b) Bringman, G.; Pokorny, F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1995; Vol. 46, p 128.
3. (c) Bhakuni, D. S.; Jain, S. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 28, p 95.
4. (a) Massiot, G.; Thepenier, P.; Jacquier, M. J.; Men-Olivier, L. L.; Verpoorte, R.; Delaude, C. Phytochemistry 1987, 26, 2839.
5. (b) Jahangir; Brook, M. A.; MacLean, D. B.; Holland, H. L. Tetrahedron 1987, 43, 5761.
6. (c) Phillipson, J. D.; Hemingway, S. R. Phytochemistry 1974, 13, 973.
7. (d) Erdelmeier, C. A.; Regenass, U.; Rali, T.; Sticher, O. Planta Med. 1992, 58, 43.
8. (e) Abreu, P.; Pereira, A. Heterocycles 1998, 48, 885.
9. (f) Arbain, D.; Putra, D. P.; Sargent, M. V. Aust. J. Chem. 1993, 46, 977.
10. (g) Caprasse, M.; Tavernier, D.; Anteunis, M. J. O.; Angenot, L. Planta Med. 1984, 50, 27.
11. (h) Arbain, D.; Lajis, N. H.; Putra, D. P.; Sargent, M. V.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1993, 46, 969.
12. (i) Arbain, D.; Byrne, L. T.; Dachriyanus; Sargent, M. V. Aust. J. Chem. 1997, 50, 1109.
13. Whaley, W. M.; Govindachari, T. R. Org. React. 1951, 6, 74.
14. Whaley, W. M.; Govindachari, T. R. Org. React. 1951, 6, 151.
15. Gensler, W. J. Org. React. 1951, 6, 191.
16. (a) Mendelson, W. L.; Spainhour, C. B., Jr.; Jones, S. S.; Lam, B. L.; Wert, K. L. Tetrahedron Lett. 1980, 21, 1393.
17. (b) Subimoto, A.; Shinba-Tanaka, H.; Ishikawa, M. Synthesis 1995, 431.
18. (c) Quallich, G. J.; Makowski, T. W.; Sander, A. F.; Urban, F. J.; Vazquez, E. J. Org. Chem. 1998, 65, 4116.
19. For reviews on lateral lithiation reactions, see: (a) Clark, R. D.; Jahangir, A. Org. React. 1995, 47, 5.
20. (b) Snieckus, V. Chem. Rev. 1990, 90, 879.
21. Davis, F. A.; Andemichael, Y. W. J. Org. Chem. 1999, 64, 8627.
22. Davis, F. A.; Mohanty, P. K.; Burns, D. M.; Andemichael, Y. W. Org. Lett. 2000, 2, 3901.
23. Davis, F. A.; Mohanty, P. K. J. Org. Chem. 2002, 67, 1290.
24. (a) Maiti, B. C.; Giri, V. S.; Pakrashi, S. C. Heterocycles 1990, 31, 847.
25. (b) Rey, A. W.; Szarek, W. A.; MacLean, D. B. Heterocycles 1991, 32, 1143.
26. (a) Ohba, M.; Kubo, H.; Fujii, T.; Ishibashi, H.; Sargent, M. V.; Arbain, D. Tetrahedron Lett. 1997, 38, 6697.
27. (b) Ohba, M.; Kubo, H.; Ishibashi, H. Tetrahedron 2000, 56, 7751.
28. Tschaen, D. M.; Desmond, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synth. Commun. 1994, 24, 887.
29. Walkup, R. E.; Linder, J. Tetrahedron Lett. 1985, 26, 2155.
30. Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403.
31. Bringmann, G.; Weirich, R.; Reuscher, H.; Jansen, J. R.; Kinzinger, L.; Ortmann, T. Liebigs Ann. Chem. 1993, 877.
32. Forbes, I. T.; Johnson, C. N.; Thompson, M. J. Chem. Soc., Perkin Trans. 1 1992, 275.