Synthesis of nicotine derivatives via reductive disilylation of (S)-nicotine

Organic Letters

Volumn 8, Issue 2, 2006, Pages 179-182

  Smith, Emilie D ^a   Février, Florence C ^a   Comins, Daniel L ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; LITHIUM; NICOTINE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; LITHIUM; MOLECULAR STRUCTURE; NICOTINE; OXIDATION-REDUCTION; SILANES; STEREOISOMERISM;

EID: 31544461208     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052099q     Document Type: Article

References (22)

1. (a) Gorrod, J. W.; Jacob, P., III Analytical Determination of Nicotine and Related Compounds and their Metabolites; Elsevier: New York, 1999.
2. (b) Pailer, M. In Tobacco Alkaloids and Related Compounds, US von Euler, Ed.; Pergamon Press: New York, 1965; p 15.
3. (a) Levin, E. D. J. Neurobiol. 2002, 53, 633.
4. (b) Newhouse, P. A.; Kelton, M. Pharm. Acta Helv. 2000, 74, 91.
5. (c) Holladay, M. K.; Dart, M. J.; Lynch, J. K. J. Med. Chem. 1997, 40, 4169.
6. (d) Breining, S. R. Curr. Top. Med. Chem. 2004, 4, 609-629.
7. (e) Jensen, A. A.; Frølund, B.; Liljefors, T.; Krosgsgaard-Larsen, P. J. Med. Chem. 2005, 48, 4705.
8. McDonald, I. A.; Vernier, J.-M.; Cosford, N.; Corey-Naeve, J. Curr. Pharm. Des. 1996, 2, 357.
9. Cosford, N. D. P.; Bleiker, L.; Dawson, H.; Whitten, J. P.; Adams, P.; Chavez-Noriega, L.; Correa, L. D.; Crona, J. H.; Mahaffy, L. S.; Menzaghi, F. M.; Rao, T. S.; Reid, R.; Sacaan, A. I.; Santori, E.; Stauderman, K.; Whelan, K.; Lloyd, G. K.; McDonald, I. A. J. Med. Chem. 1996, 39, 3235.
10. Tschitschibabin, A. E.; Kirssanow, A. W. Chem. Ber. 1924, 57, 1163.
11. Rhondahl, L. Acta Pharm. Suec. 1997, 14, 113.
12. (a) Seeman, J. I.; Secor, H. V.; Howe, C. R.; Chavdarian, C. G.; Morgan, L. W. J. Org. Chem. 1983, 48, 4899 and references therein.
13. (b) Also see: Seeman, J. I.; Chavdarian, C. G.; Kornfeld, R. A.; Nworal, J. D. Tetrahedron 1985, 41, 595.
14. Wang, D. X.; Booth, H.; Lerner-Marmarosh, N.; Osdene, T. S.; Abood, L. G. Drug Dev. Res. 1998, 45, 10.
15. Garvey, D. S.; Wasicak, J. T.; Elliot, R. L.; Lebold, S. A.; Hettinger, A.-M.; Carrera, G. M.; Lin, N.-H.; He, Y.; Holladay, M. W.; Anderson, D. J.; Cadman, E. D.; Raszkiewicz, J. L.; Sullivan, J. P.; Aneric, S. P. J. Med. Chem. 1994, 37, 4455.
16. Sulzbach, R. A. J. Organomet. Chem. 1970, 24, 307.
17. (a) Tsuge, O.; Kanemasa, S.; Naritomi, T.; Tanaka, J. Chem. Lett. 1984, 1255.
18. (b) Tsuge, O.; Kanemasa, S.; Naritomi, T.; Tanaka, J. Bull. Chem. Soc. Jpn. 1987, 60, 1497.
19. This was determined by conversion of 7 to enantiopure 18 (98% ee by chiral column HPLC). See Scheme 3.
20. (a) Comins, D. L.; Despagnet, E. U.S. Patent Application 10/925,516.
21. (b) King, L. S.; Smith, E.; Comins, D. L. U.S. Patent Application 10/715,147.
22. For 2.2′-bipyridine ligands prepared from nicotine, see: Schmidt, B.; Neitemeier, V. Synthesis 1998, 42.