Synthesis of (+)- and (-)-N-BOC-7-Azabicyclo[2.2.1]heptan-2-ones, Versatlle Intermediates for the Enantiospecific Synthesis of (+)- and (-)-Epibatidine and Analogues

Journal of Organic Chemistry

Volumn 60, Issue 9, 1995, Pages 2683-2691

  Hernández, Andrés ^a   Marcos, Manuel ^a   Rapoport, Henry ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 AZABICYCLO[2.2.1]HEPTANE DERIVATIVE; EPIBATIDINE; NORBORNANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029045992     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00114a015     Document Type: Article

References (39)

1. Spande, T. F.; Garraffo, M. H.; Edwards, M. W.; Yeh, H. J. C.; Pannel, L.; Daly, J. W. J. Am. Chem. Soc. 1992, 114, 3475.
2. Li, T.; Quian, C.; Eckman, J.; Huang, D. F.; Shen, T. Y. Bioorg. Med. Chem. Lett. 1993, 3, 2759.
3. Fletcher, S. R.; Baker, R.; Chambers, M. S.; Herbert, R. H.; Hobbs, S. C.; Thomas, S. R.; Verrier, H. M.; Watt, A. P.; Ball, R. G. J. Org. Chem. 1994, 59, 1771; and refs 4 and 5 therein.
4. Huang, D. F.; Shen, T. Y. Tetrahedron Lett. 1993, 34, 4477.
5. Broka, C. A. Tetrahedron Lett. 1993, 34, 3251.
6. Corey, E. J.; Loh, T.-P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600.
7. Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay, Jr., C.; Temesvári-Major, E.; Blaskó, G. Tetrahedron Lett. 1994, 35, 3171.
8. Sestanj, K.; Melenski, E.; Jirkovsky, I. Tetrahedron Lett. 1994, 35, 5417.
9. Ko, S. Y.; Lerpiniere, J.; Linney, I. D.; Wrigglesworth, R. J. Chem. Soc. Chem. Commun. 1994, 1775.
10. Clayton, S. C.; Regan, A. C. Tetrahedron Lett. 1993, 34, 7493.
11. Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N. Synlett. 1994, 343.
12. Okabe, K.; Natsume, M. Chem. Pharm. Bull. 1994, 42, 1432.
13. Petersen, J. S.; Fels, G.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 4539; and ref 4a therein
14. Sardina, J. F.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025.
15. Hernandez, A.; Rapoport, H. J. Org. Chem. 1994, 59, 1058.
16. Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230 and refs 12-15 therein.
17. Davis, F. A.; Vishwakarma, L. C.; Billmers, J. M.; Finn, J. J. Org. Chem. 1984, 49, 3241.
18. Vishwakarma, L. C.; Stringer, O. D.; Davis, F. A. Org. Synth. 1988, 66, 203.
19. Davis, F. A.; Chattopadhyay, S.; Towson, J. C.; Lai, S.; Reddy, T. J. Org. Chem. 1988, 53, 2087.
20. Belletire, J. L.; Fry, D. F. J. Org. Chem. 1988, 53, 4724.
21. Anderson, A. G.; Stang, P. J. J. Org. Chem. 1976, 41, 3034.
22. Stang, P. J.; Fisk, T. E. Synthesis 1979, 438.
23. Anderson, A. G.; Stang, P. J. Org. Synth. 1981, 60, 34.
24. Sardina, J. F.; Howard, M. H.; Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 4654.
25. Shafi'ee, A.; Hite, G. J. Org. Chem. 1968, 33, 3435.
26. Fraser, R. R.; Swingle, R. B. Can. J. Chem. 1970, 48, 2065.
27. Slougui, N.; Rousseau, G.; Conia, J.-M. Synthesis 1982, 58.
28. Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1976, 41, 1396.
29. Yanuka, Y.; Katz, R.; Sarel, S. Tetrahedron Lett. 1968, 1725.
30. Beebe, T. R.; Adkins, R. L.; Belcher, A. I.; Choy, T.; Fuller, A. E.; Morgan, V. L.; Sencherey, B. B.; Russell, L. J.; Yates, S. W. J. Org. Chem. 1982, 47, 3006.
31. Howard, M. H.; Sardina, F. J.; Rapoport, H. J. Org. Chem. 1990, 55, 2829.
32. Barton, D. H. R.; Hervé Y.; Potier, P.; Thierry, J. Tetrahedron 1988, 44, 5479.
33. Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316.
34. Heathcock, C. H.; Young, S. D.; Hagen, J. P.; Pilli, R.; Bad-ertscher, U. J. Org. Chem. 1985, 50, 2095.
35. Trost, B. M.; Tamaru, Y. J. Am. Chem. Soc. 1977, 99, 3101.
36. Fessner, W.-D.; Sedelmeier, G.; Spurr, P. R.; Rihs, G.; Prinzbach, H. J. Am. Chem. Soc. 1987, 109, 4626.
37. Okamoto, S.; Harada, T.; Tai, A. Bull. Chem. Soc. Jpn. 1993, 56, 1414.
38. Barton, D. H. R.; Bridon, D.; Fernandez-Picot, I.; Zard, S. Z. Tetrahedron 1987, 43, 2733.
39. Stevens, R. V.; Beaulieu, N.; Chah, W. H.; Daniewski, A. R.; Takeda, T.; Waldner, A.; Williard, P. G.; Zutter, U. J. Am. Chem. Soc. 1986, 108, 1039.