Total synthesis of (±) epibatidine

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1463-1466

  Xu, Rui ^a   Chu, Guohua ^a   Bai, Donglu ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EPIBATIDINE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029920516     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00042-1     Document Type: Article

References (27)

1. Spande, T.F.; Garraffo, H.M.; Edwards, M.W.; Yeh, H.J.C.; Pannel, L.; Daly, J.W., J. Am. Chem. Soc., 1992, 114, 3475-3478.
2. Qian, C.; Li, T.; Shen, T.Y.; Libertine-Garaham, L.; Eckman, J.; Biftu, T.; Ip, S., Eur. J. Pharmacol., 1993, 250, R13-R14.
3. Badio, B.; Daly, J.W., Mol. Pharmcol., 1994, 45, 563-569.
4. Li, T.; Qian, C.; Eckman, J.; Huang, D.F.; Shen, T.Y., Bioorg. Med. Chem. Lett., 1993, 3, 2759-2764.
5. Huang, D.F.; Shen, T.Y., Tetrahedron Lett., 1993, 34, 4477-4480.
6. Clayton, S.C.; Regan, A.C., Tetrahedron Lett., 1993, 34, 7493-7496.
7. Okabe, K.; Natsume, M., Chem. Pharm. Bull., 1994, 42, 1432-1436.
8. Kotian, P.L.; Carrol, F.I., Synth. Commun., 1995, 25, 63-71.
9. Broka, C.A., Tetrahedron Lett., 1993, 34, 3251-3254.
10. Fletcher, S.R.; Baker, R.; Chambers, M.S.; Hobbs, S.C.; Mitchell, P.J., J. Chem. Soc., Chem. Commun., 1993, 1216-1218.
11. Corey, E.J.; Loh, T.E.; AchyuthaRao, S.; Daley, D.C.; Sarshar, S., J. Org. Chem., 1993, 58, 5600-5602.
12. 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, 1771-1778.
13. Szántay, C.; Kardos-Balogh, Z.; Moldvai, I.; Szántay Jr., C.; Major-Temesváry, E.; Blaskó, G., Tetrahedron Lett., 1994, 35, 3171-3174.
14. Senokuchi, K.; Nakai, H.; Kawamura, M.; Katsube, N.; Nonaka, S.; Sawaragi, H.; Hamanaka, N., Synlett, 1994, 343-344.
15. Sestanj, K.; Melenski, E.; Jirkovsky, I., Tetrahedron Lett., 1994, 35, 5417-5420.
16. Ko, S.Y.; Lerpiniere, J.; Linney, I.D.; Wrigglesworth, R., J. Chem. Soc., Chem. Commun., 1994, 1775-1776.
17. Albertini, E.; Barco, A.; Benetti, S.; Risi, C.D.; Pollini, G.P.; Romagnoli, R.; Zanirato, V., Tetrahedron Lett., 1994, 35, 9297-9300.
18. Itooka, T.; Matoba, K.; Yamazaki, T.; Muraoka, O.; Momose, T., Chem. Pharm. Bull., 1986, 34, 2391-2396.
19. Montzka, T.A.; Matiskella, J.D.; Rartyka, R.A., Tetrahedron Lett., 1974, 15, 1325-1327.
20. Bauer, D.P.; Macomber, R.S., J. Org. Chem., 1975, 40, 1990-1992.
21. Chenier, P.J.; Kao, J.C., J. Org. Chem., 1976, 41, 3730-3734.
22. Magidson, O.; Menschikoff, G., Chem. Ber., 1925, 58, 113-118.
23. Arcadi, A.; Marinelli, F.; Bernocchi, E.; Cacchi, S.; Ortar, G.J., J. Organometallic Chem., 1989, 368, 249-256.
24. Larock, R.C.; Johnson, P.L., J. Chem. Soc., Chem. Commun., 1989, 1368-1370.
25. Gonzalez, J.; Koontz, J.I.; Hodges, L.M.; Nilsson, K.R.; Neely, L.K.; Myers, W.H.; Sabat, M.; Harman, W.D., J. Am. Chem. Soc., 1995, 117, 3405-3421.
26. Barton, D.H.R.; Crich, D.; Motherwell, W.B., Tetrahedron, 1985, 41, 3901-3924.
27. 3) δ 8.26 (1H, d, J=2.4Hz), 7.77 (1H, dd, J=8.3Hz, 2.4Hz), 7.23 (1H, d, J=8.3Hz), 3.83 (1H, m), 3.59 (1H, br s), 2.79 (1H, dd, J=8.8Hz,.5.3Hz), 1.92 (1H, dd, J=12.2Hz, 9.1Hz), 1,4-1.8 (5H, m).