An intramolecular radical approach to angular electrophores in polycyclic systems

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1751-1754

  Zoretic, Phillip A ^a   Zhang, Yongzheng ^a   Ribeiro, Anthony A ^b  

^a EAST CAROLINA UNIVERSITY   (United States)

^b DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029986721     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00167-0     Document Type: Article

References (27)

1. (a). Geise, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford and New York, 1986;
2. (b). Ramaiah, M. Tetrahedron 1987, 43, 3541;
3. (c). Curran, D. P. Synthesis 1988, 417 and 489;
4. (d). Surzur, J.-M.; Bertrand, M. P. Pure Appl. Chem. 1988, 60, 1659;
5. (e). Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991,91, 1237;
6. (f). Porter, N. A.; Giese, B.; Curran, D. P. Acc. of Chem. Res. 1991, 24, 296;
7. (g). RajanBabu, T. V. ibid. 1991, 24, 139;
8. (h). Melikyan, G. G. Synthesis 1993, 833;
9. (i). Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
10. Breslow, R.; Olin, S. S.; Groves, J. T. Tetrahedron Lett. 1968, 1837; and references within.
11. Lallemand, J. Y.; Julia, M.; Mansuy, D. Tetrahedron Lett. 1973, 4461.
12. Snider, B. B.; Mohan, R.; Kates, S. A. Tetrahedron Lett. 1987, 28, 841.
13. Zoretic, P. A.; Wang, M.; Zhang, Y.; Shen, Z.; Ribeiro, A. A. J. Org. Chem. in press.
14. Zoretic, P. A.; Shen, Z.; Wang, M.; Ribeiro, A. A. Tetrahedron Lett. 1995, 36, 2925.
15. Zoretic, P. A.; Zhang, Y; Ribeiro, A. A. Tetrahedron Lett. 1995, 36, 2929.
16. Zoretic, P. A.; Weng, Y; Caspar, M. L.; Davis, D. G. Tetrahedron Lett. 1991, 32, 4819.
17. Umbreit, M. A.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 5526.
18. Julia, M.; Julia, S.; Guegan, R. Bull. Soc. Chim. Fr. 1960, 1072.
19. Takayanagi, H. Tetrahedron Lett. 1994, 35, 1581.
20. All new compounds gave satisfactory spectral and analytical data.
21. Hagashi, H.; Nakanishi, K.; Brandon, C.; Marmur, J. J. Am. Chem. Soc. 1973, 95, 8749; and references within.
22. Huckin, S. N.; Weiler, L. J. J. Am. Chem. Soc. 1974, 96, 1082.
23. 3, δ) for other compounds in this work are: 2 5.44(m, 1H), 4.02(s, 2H), 3.39(t, 2H), 1.68(s, 3H); 3 5.45(m, 1H), 4.61(br t, 1H), 4.12(d, 1H, J=12 Hz), 3.87(d, 1H, J=12Hz), 3.37(t, 2H), 1.68(s, 3H); 4 5.38(m, 1H), 2.94(dt, 1H, J=7.8, 23.0 Hz), 1.71(s, 3H), 1.39(t, 6H, J=7.1 Hz); 5 6.13(t, 1H, J=7.6 Hz), 5.79(m, 1H), 5.36(m, 1H), 4.94-5.13(m, 2H), 4.11 (d, 1H, J=11.9 Hz), 3.84(d, 1H, J=11.8 Hz), 1.67(s, 3H); 6 6.15(t, 1H, J=7.7 Hz), 5.80(m, 1H), 5.37(m, 1H), 4.00(br s, 2H), 1.68(s, 3H); 7 6.14(t, 1H, J=7.7 Hz), 3.95(s, 2H), 1.78(s, 3H); 8 6.12(t, 1H, J=7.5Hz), 4.19(q, 2H), 3.51(q, 1H), 1.33(d, J=7.2 Hz) and 1.27(t, J=7.1 Hz)[6H].
24. Dombroski, M. A.; Kates, S. A.; Snider, B. B. J. Am. Chem. Soc. 1990, 112, 2759.
25. 3).
26. Kazlauskas, R.; Murphy, P. T.; Wells, R. J.; Noack, K.; Oberhansli, W. E.; Schonholzer, P. Aust. J. Chem. 1979, 32, 867; Gunasekera, S. P.; Schmitz, F. J. J. Org. Chem. 1990, 56, 250.
27. Kazlauskas, R.; Murphy, P. T.; Wells, R. J.; Noack, K.; Oberhansli, W. E.; Schonholzer, P. Aust. J. Chem. 1979, 32, 867; Gunasekera, S. P.; Schmitz, F. J. J. Org. Chem. 1990, 56, 250.