Tandem radical cyclisations leading to indolizidinones and pyrrolizidinones

Tetrahedron Letters

Volumn 39, Issue 39, 1998, Pages 7197-7200

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

^a UNIVERSITY OF YORK   (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

Alkaloids; Bicyclic heterocyclic compounds; Cyclisation; Tin and compounds

Indexed keywords

ALKALOID DERIVATIVE; INDOLIZIDINONE; PYRROLIZIDINE DERIVATIVE; PYRROLIZIDINONE; UNCLASSIFIED DRUG;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CANCER; CATTLE DISEASE; CYCLIZATION;

BOS TAURUS;

EID: 0032563822     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01542-1     Document Type: Article

References (26)

1. 1. (a) Michael, J.P. Nat. Prod. Rep., 1997, 14, 619.
2. (b) J.R. Liddell, Nat. Prod. Rep., 1996, 13, 187.
3. 2. For examples of recent synthetic approaches see: (a) Denmark, S.E.; Parker, D.L.; Dixon, J.A. J. Org. Chem., 1997, 62, 435.
4. (b) McAlonan, H.; Stevenson, P.J.; Thompson, N.; Treacy, A.B. Synlett, 1997, 1359.
5. (c) Li, Y; Marks, T.J. J. Am. Chem. Soc., 1998, 120, 1757.
6. (d) Arisawa, M.; Takezawa, E.; Nishida, A.; Mori, M.; Nakagawa, M. Synlett, 1997, 1179.
7. (e) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761.
8. (f) Carretero, J.C.; Arráyas, R.G. J. Org. Chem., 1998, 63, 2993.
9. 3. (a) Baker, S.R.; Parsons, A.F.; Wilson, M. Tetrahedron Lett., 1998, 39, 2815.
10. (b) Goodall, K.; Parsons, A.F. J. Chem. Soc., Perkin Trans. 1, 1994, 3257.
11. (c) Goodall, K.; Parsons, A.F. Tetrahedron, 1996, 52, 6739.
12. (d) Goodall, K.; Parsons, A.F. Tetrahedron Lett., 1997, 38, 491.
13. 4. (a) Beckwith, A.L.J.; Schiesser, C.H. Tetrahedron, 1985, 41, 3925.
14. (b) Spellmeyer, D.C.; Houk, K.N. J. Org. Chem., 1987, 52, 959.
15. 2O, -10 to 0°C) of 3-butenenitrile and trans-3-pentenenitrile (95%) respectively.
16. 6. Davies, D.T; Goodall, K.; Kapur, N.; O'Brien, M.; Parsons, A.F. Synth. Commun., 1997, 27, 3815.
17. 7. All new compounds exhibited satisfactory spectral and analytical (high resolution mass) data.
18. 8. (a) Hart, D.J.; Tsai, Y.M. J. Am. Chem. Soc., 1982, 104, 1430.
19. (b) Burnett, D.A.,; Choi, J-K.; Hart, D.J.; Tsai, Y-M. J. Am. Chem. Soc., 1984, 106, 8201.
20. (c) Hart, D.J.; Tsai, Y-M. J. Am. Chem. Soc., 1984, 106, 8209.
21. 1H-13C coupling constants but because of spectral overlap the assignment was not totally unambiguous.
22. 1H-13C coupling constants were consistent with the stereochemistry as drawn but an unambiguous assignment was not possible because of spectral overlap.
23. 11. For a related cyclisation see Sato, T.; Nakamura, N.; Ikeda, K.; Okada, M.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. I, 1992, 2399.
24. 12. See for example Hernández, A.S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem., 1996, 61, 314.
25. 13. (a) Martín-López, M.J.; Bermejo-González, F. Tetrahedron Lett., 1994, 35, 4235 and 8843.
26. (b) Rodríquez, R.; Bermejo, F. Tetrahedron Lett., 1996, 37, 5581.