A new entry to 9-azabicyclo[3.3.1]nonanes using radical translocation/cyclisation reactions of 2-(but-3-ynyl)-1-(o-iodobenzoyl)piperidines

Journal of the Chemical Society. Perkin Transactions 1

Volumn 2, Issue 12, 2002, Pages 1438-1443

  Sato, Tatsunori ^a   Yamazaki, Taro ^a   Nakanishi, Yumi ^a   Uenishi, Jun Ichi ^a   Ikeda, Masazumi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CHLORINE COMPOUNDS; CHROMATOGRAPHY; ESTERS; FREE RADICALS; HYDRIDES; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PHOSPHORUS COMPOUNDS; STRUCTURE (COMPOSITION); TOLUENE;

AZABICYCLONONANES; AZOISOBUTYRONITRILE; BUTYNYL IODOBENZOYLPIPERIDINES; CARBONYL GROUP; CYCLIZATION; DESILYLATION; EUPHOCOCCININE; POTASSIUM TERT-BUTOXIDE; RADICAL TRANSLOCATION; TRIBUTYLTIN HYDRIDE;

SYNTHESIS (CHEMICAL);

EID: 0035996258     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b203243k     Document Type: Article

References (36)

1. T. Sato, T. Mori, T. Sugiyama, H. Ishibashi, M. Ikeda Heterocycles 1994, 37, 245.
2. T. Sato, Y. Kugo, E. Nakaumi, H. Ishibashi, M. Ikeda J. Chem. Soc., Perkin Trans. 1 1995, 1801.
3. M. Ikeda, Y. Kugo, T. Sato J. Chem. Soc., Perkin Trans. 1 1996, 1819.
4. M. Ikeda, Y. Kugo, Y. Kondo, T. Yamazaki, T. Sato J. Chem. Soc., Perkin Trans. 1 1997, 3339.
5. M. Ikeda, M. Hamada, S.A.A. El Bialy, K. Matsui, S. Kawakami, Y. Nakano, S.M.M. Bayomi, T. Sato Heterocycles 2000, 52, 571.
6. T. Sato, K. Okamoto, Y. Nakano, J. Uenishi, M. Ikeda Heterocycles 2001, 54, 747.
7. V. Snieckus, J.-C. Cuevas, C.P. Sloan, H. Liu, D.P. Curran J. Am. Chem. Soc. 1990, 112, 896.
8. D.P. Curran, W. Shen J. Am. Chem. Soc. 1993, 115, 6051.
9. D.P. Curran, H. Liu J. Chem. Soc.
10. F. Beaulieu, J Arora, U. Veith, N.J. Taylor, B.J. Chapell, V. Snieckus J. Am. Chem. Soc. 1996, 118, 8727.
11. Y. Hamada, N. Okamoto, O. Hara Heterocycles 2000, 52, 929.
12. R. K. Hill, L.A. Renbaum Tetrahedron 1982, 38, 1959.
13. D.H. Gnecco Medina, D.S. Grierson, H.-P. Husson Tetrahedron Lett. 1983, 24, 2099.
14. C. Yue, J. Royer, H.-P. Husson J. Org. Chem. 1992, 57, 4211.
15. E.C. Davison, A.B. Holmes Tetrahedron Lett. 1995, 36, 9047.
16. A.B. Holmes, B. Bourdin, I. Collins, E.C. Davison, A.J. Rudge, T.C. Stork, J.A. Warner Pure Appl. Chem. 1997, 69, 531.
17. S.-I. Murahashi, J. Sun, H. Kurosawa, Y. Imada Heterocycles 2000, 52, 531.
18. M.F. Mechelke, A.I. Meyers Tetrahedron Lett. 2000, 41, 4339.
19. A. Hassner, R. Maurya, A. Padwa, W.H. Bullock J. Org. Chem. 1991, 56, 2775.
20. F. Johnson Chem. Rev. 1968, 68, 375.
21. R.W. Hoffmann Chem. Rev. 1989, 89, 1841.
22. M. Natsume, M. Ogawa Chem. Pharm. Bull. 1982, 30, 3442.
23. N.K. Hart, S.R. Johns, J.A. Lamberton Aust. J. Chem. 1967, 20, 561.
24. W.V. Brown, B.P. Moore Aust. J. Chem. 1982, 35, 1255.
25. T. Eisner, M. Goetz, D. Aneshausley, G. Ferstandig-Arnold, J. Meinwald Experientia 1986, 42, 204.
26. V.V. Kane, V. Singh, A. Martin, D.L. Doyle Tetrahedron 1983, 39, 345.
27. E.M. Burgess, H.R. Penton, Jr., E.A. Taylor J. Org. Chem. 1973, 38, 26.
28. J.C. Martin, R.J. Arhart J. Am. Chem. Soc. 1971, 93, 4327.
29. B.H. Lipshutz, D.J. Buzard and R.W. Vivian, Tetrahedron Lett., 1999, 40, 6871..
30. D.L. Comins, A. Dehghani Tetrahedron Lett. 1992, 33, 6299.
31. S.V. Ley, J. Norman, W.P. Griffith, S.P. Marsden Synthesis 1994, 639.
32. W.J. Scott, J.K. Stille J. Am. Chem. Soc. 1986, 108, 3033.
33. W.J. Scott, J.E. McMurry Acc. Chem. Res. 1988, 21, 47.
34. K. Ritter Synthesis 1993, 735.
35. H. Kotsuki, P.K. Datta, H. Hayakawa, H. Suenaga Synthesis 1995, 1348.
36. J.E. McMurry, W.J. Scott Tetrahedron Lett. 1983, 24, 979.