A concise stereoselective synthesis of epibatidine employing conjugate addition to an alkenyl sulfone intermediate as the key step

Synlett

Volumn , Issue 5, 1997, Pages 589-590

  Giblin, Gerrard M P ^a   Jones, Clifford D ^b   Simpkins, Nigel S ^b  

^a GLAXOSMITHKLINE   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002761788     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3225     Document Type: Article

References (18)

1. Spande, T. F.; Garraffo, H. M.; Edwards, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. J. Am. Chem. Soc. 1992, 114, 3475.
2. (a) For a recent review, see Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179.
3. (b) For a very recent formal synthesis, see Albertini, E.; Barco, A.; Benetti, S.; De Risi, C.; Pollini, G. P.; Zanirato, V. Tetrahedron Lett. 1997, 38, 681.
4. For enantioselective syntheses, see (a) Trost, B. M.; Cook, G. R. Tetrahedron Lett. 1996, 37, 7485.
5. (b) Szántay, C.; Kardos Balogh, Z.; Moldvai, I.; Szántay Jr., C.; Temesvári-Major. E.; Blaskó, G. Tetrahedron 1996, 52, 11053. See also reference 2(b).
6. For related cycloaddition approaches, see (a) Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477.
7. (b) Clayton, S. C.; Regan, A. C.; Tetrahedron Lett. 1993, 34, 7493.
8. (c) Kotian, P. L.; Carroll, F. I. Synth. Commun. 1995, 25, 63.
9. (d) Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189.
10. (a) Altenbach, H. J.; Constant, D.; Martin, H-D.; Mayer, B.; Müller, M.; Vogel, E Chem. Ber. 1991, 124, 791.
11. (b) Chen, Z.; Trudell, M. L. Tetrahedron Lett. 1994, 35, 9649. See also reference 4.
12. The pyridines used were 5-bromo-2-methoxypyridine and 2-chloro-5-iodopyridine.
13. 5S requires M, 459.1954).
14. 2Me series of compounds were both employed in the early parts of this study, but later work, which enabled the completion of the synthesis utilised the N-Boc series.
15. Other syntheses of epibatidine have utilised this transformation, see (a) Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417.
16. (b) Okabe, K.; Natsume, M. Chem. Pharm. Bull. 1994, 42, 1432.
17. 35Cl requires M, 208.0762).
18. Szántay, C.; Kardos Balogh, Z.; Moldvai, I.; Szántay Jr., C.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171.