Tandem radical cyclisation of enamides mediated by tin hydride; pyrrolizidinone or indolizidinone ring formation

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 4, 1999, Pages 427-436

  Richard Baker, S ^a   Burton, Keith I ^b   Parsons, Andrew F ^b   Pons, Jean François ^b   Wilson, Michelle ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746525673     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (15)

1. F. Aldabbagh, and W. R. Bowman, Contemp. Org. Synth., 1997,261; B. Giese, B. Kopping, T. Göbel, J. Dickhaut, G. Thoma, K. J. Kulicke, and F. Trach, Org. React. (NY), 1996, 48, 301; A. G. Fallis, and I. M. Brinza, Tetrahedron, 1997, 53, 17543.
2. For recent examples see: J. Quirante, C. Escolano, A. Merino, and J. Bonjoch, J. Org. Chem., 1998, 63, 968; D. L. J. Clive, and V. S. C. Yeh, Tetrahedron Lett., 1998, 39, 4789; C. K. McClure, A. J. Kiessling, and J. S. Link, Tetrahedron, 1998,54, 7121; R. Giovannini, and M. Petrini, Synlell, 1998, 90; D. L. Boger, C. W. Boyce, R. M. Garbaccio, and M. Searcey, Tetrahedron Lett., 1998, 39, 2227; J. Cossy, M. Cases, and D. Gomez Pardo, Tetrahedron Lett., 1998, 39, 2331; V. Gupta, M. Besev, and L. Engman, Tetrahedron Lett., 1998,39,2429; P. Mangeney, L. Hamon, S. Raussou, N. Urbain, and A. Alexakis, Tetrahedron, 1998,54, 10349; D. L. J. Clive, and D. M. Coltart, Tetrahedron Lett., 1998.39V2519.
3. H. Ishibashi, N. Nakamura, T. Sato, M. Takeuchi, and M. Ikeda, Tetrahedron Lett., 1991,32, 1725; T. Sato, N. Nakamura, K. Ikeda, M. Okada, H. Ishibashi, and M. Ikeda, J. Client. Soc., Perkin Trans, l, 1992,2399.
4. H. Ishibashi, M. Higuchi, M. Ohba, and M. Ikeda, Tetrahedron Lett., 1998, 39, 75; M. Ikeda, S. Ohtani, T. Yamamoto, T. Sato, and H. Ishibashi, J. Client. Soc., Perkin Trans, l, 1998, 1763; H. Ishibashi, Y. Fuke, T. Yamashita, and M. Ikeda, Tetrahedron: Asymmetry, 1996, 7, 2531; T. Sato, N. Chono, H. Ishibashi, and M. Ikeda, J. Client. Soc, Perkin Trans. 1, 1995, 1115; T. Sato, N. Machigashira, H. Ishibashi, and M. Ikeda, Heterocycles, 1992, 33, 139; H. Ishibashi, T. Nakaharu, M. Nishimura, A. Nishikawa, C. Kameoka, and M. Ikeda, Tetrahedron, 1995,51,2929.
5. J. Cassayre, B. Quiclet-Sire, J.-B. Saunier, and S. Z. Zard, Tetrahedron, 1998, 54, 1029; J. Cassayre, B. Quiclet-Sire, J.-B. Saunier, and S. Z. Zard, Tetrahedron Lett., 1998,39,8995. '
6. D. T. Davies, N. Kapur, and A. F. Parsons, Tetrahedron Lett., 1998, 39,4397.
7. K. Goodall, and A. F. Parsons, J. Chan. Soc., Perkin Trans, l, 1994, 3257; K. Goodall, and A. F. Parsons, Tetrahedron, 1996, 52, 6739.
8. S. R. Baker, A. F. Parsons, and M. Wilson, Tetrahedron Lett., 1998, '39,2815.
9. K. Goodall, and A. F. Parsons, Tetrahedron Lett., 1997,38,491.
10. Part of this work has appeared as a preliminary communication: S. R. Baker, A. F. Parsons, J.-F. Pons, and M. Wilson, Tetrahedron Lett., 1998,39,7179.
11. J. P. Michael, Nat. Prod. Rep., 1997,14,619; J. R. Liddell, Nat. Prod. Rep., 1996,13, 187.
12. D. T. Davies, K. Goodall, N. Kapur, M. O'Brien, and A. F. Parsons, Synth. Commun., 1997, 27, 3815.
13. D. J. Hart, and Y. M. Tsai, J. Am. Chem. Soc., 1982, 104, 1430; D. A. Burnett, J.-K. Choi, D. J. Hart, and Y.-M. Tsai, J. Am. Chem. Soc., 1984,106,8201; D. J. Hart, and Y.-M. Tsai, J. Am. Chem. Soc., 1984,106, 8209.
14. A. L. J. Beckwith, G. E. Gream, and D. L. Struble, Amt. J. Chem., 1972,25, 1081; M. Julia, PurcAppl. Chem., 1967,15, 167.
15. E. W. Thomas, R. H. Rynbrandt, D. C. Zimmermann, L. T. Bell, C. R. Muchmore, and E. W. Yankee, J. Org. Chem., 1989, 54, 4535; C. Cox, V. G. Young, Jr., and T. Lectka, J. Am. Chem. Soc., 1997, 119,2307. 16 K. Matsumotoand K. Harada,.J. Org. Chem., 1966,31, 1956.