Enaminones as intermediates in the synthesis of indolizidine alkaloids

Pure and Applied Chemistry

Volumn 69, Issue 3, 1997, Pages 583-588

  Michael, Joseph P ^a   Gravestock, David ^a  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001263366     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199769030583     Document Type: Article

References (33)

1. J.W. Daly, H.M. Garraffo and T.F. Spande, Alkaloids (N.Y.) 43, 185 (1993).
2. J.W. Daly, Y. Nishizawa, W.L. Padgett, T. Tokuyama, A.L. Smith, A.B. Holmes, C. Kibayashi and R.S. Aronstam, Neurochem. Res. 16, 1213 (1991).
3. J.P Michael and A.S. Parsons, Tetrahedron 52, 2199 (1996); and references cited therein.
4. A.B. Holmes, A.L. Smith, S.F. Williams, L.R. Hughes, Z. Lidert and C. Swithenbank, J. Org. Chem. 56, 1393 (1991).
5. D. Gnecco, C. Marazano and B.C. Das, J. Chem. Soc., Chem. Commun. 625 (1991).
6. For other syntheses of indolizidine 209B using an N-C3 disconnection, see the following: D.L. Comins and E. Zeller, Tetrahedron Lett. 32, 5889 (1991); Y. Shishido and C. Kibayashi, J. Org. Chem. 57, 2876 (1992); A. Satake and I. Shimizu, Tetrahedron: Asymmetry 4, 1405 (1993); T. Momose and N. Toyooka, J. Org. Chem. 59, 943 (1993); J. Åhman and P. Somfai, Tetrahedron 51, 9747 (1995). For syntheses of indolizidine 209B using alternative disconnections see J. Aubé, P.S. Rafferty and G.L. Milligan, Heterocycles 35, 1141 (1993); and ref. 12.
7. For other syntheses of indolizidine 209B using an N-C3 disconnection, see the following: D.L. Comins and E. Zeller, Tetrahedron Lett. 32, 5889 (1991); Y. Shishido and C. Kibayashi, J. Org. Chem. 57, 2876 (1992); A. Satake and I. Shimizu, Tetrahedron: Asymmetry 4, 1405 (1993); T. Momose and N. Toyooka, J. Org. Chem. 59, 943 (1993); J. Åhman and P. Somfai, Tetrahedron 51, 9747 (1995). For syntheses of indolizidine 209B using alternative disconnections see J. Aubé, P.S. Rafferty and G.L. Milligan, Heterocycles 35, 1141 (1993); and ref. 12.
8. For other syntheses of indolizidine 209B using an N-C3 disconnection, see the following: D.L. Comins and E. Zeller, Tetrahedron Lett. 32, 5889 (1991); Y. Shishido and C. Kibayashi, J. Org. Chem. 57, 2876 (1992); A. Satake and I. Shimizu, Tetrahedron: Asymmetry 4, 1405 (1993); T. Momose and N. Toyooka, J. Org. Chem. 59, 943 (1993); J. Åhman and P. Somfai, Tetrahedron 51, 9747 (1995). For syntheses of indolizidine 209B using alternative disconnections see J. Aubé, P.S. Rafferty and G.L. Milligan, Heterocycles 35, 1141 (1993); and ref. 12.
9. For other syntheses of indolizidine 209B using an N-C3 disconnection, see the following: D.L. Comins and E. Zeller, Tetrahedron Lett. 32, 5889 (1991); Y. Shishido and C. Kibayashi, J. Org. Chem. 57, 2876 (1992); A. Satake and I. Shimizu, Tetrahedron: Asymmetry 4, 1405 (1993); T. Momose and N. Toyooka, J. Org. Chem. 59, 943 (1993); J. Åhman and P. Somfai, Tetrahedron 51, 9747 (1995). For syntheses of indolizidine 209B using alternative disconnections see J. Aubé, P.S. Rafferty and G.L. Milligan, Heterocycles 35, 1141 (1993); and ref. 12.
10. For other syntheses of indolizidine 209B using an N-C3 disconnection, see the following: D.L. Comins and E. Zeller, Tetrahedron Lett. 32, 5889 (1991); Y. Shishido and C. Kibayashi, J. Org. Chem. 57, 2876 (1992); A. Satake and I. Shimizu, Tetrahedron: Asymmetry 4, 1405 (1993); T. Momose and N. Toyooka, J. Org. Chem. 59, 943 (1993); J. Åhman and P. Somfai, Tetrahedron 51, 9747 (1995). For syntheses of indolizidine 209B using alternative disconnections see J. Aubé, P.S. Rafferty and G.L. Milligan, Heterocycles 35, 1141 (1993); and ref. 12.
11. For other syntheses of indolizidine 209B using an N-C3 disconnection, see the following: D.L. Comins and E. Zeller, Tetrahedron Lett. 32, 5889 (1991); Y. Shishido and C. Kibayashi, J. Org. Chem. 57, 2876 (1992); A. Satake and I. Shimizu, Tetrahedron: Asymmetry 4, 1405 (1993); T. Momose and N. Toyooka, J. Org. Chem. 59, 943 (1993); J. Åhman and P. Somfai, Tetrahedron 51, 9747 (1995). For syntheses of indolizidine 209B using alternative disconnections see J. Aubé, P.S. Rafferty and G.L. Milligan, Heterocycles 35, 1141 (1993); and ref. 12.
12. A.S. Howard, G.C. Gerrans and J.P. Michael, J. Org. Chem. 45, 1713 (1981).
13. J.P. Michael and C.M. Jungmann, Tetrahedron 48, 10211 (1992).
14. J.P. Michael, S.S.-F. Chang and C. Wilson, Tetrahedron Lett. 34, 8365 (1993).
15. K. Shiosaki. In Comprehensive Organic Synthesis (B.M. Trost, ed.), Vol. 2, pp 865-892. Pergamon Press, Oxford (1991).
16. R.V. Stevens, Acc. Chem. Res. 17, 289 (1984).
17. C.W. Jefford, K. Sienkiewicz and S.R. Thornton, Helv. Chim. Acta 78, 1511 (1995).
18. Dr C. Marazano, CNRS, Gif-sur-Yvette, personal communication. We are grateful to Dr Marazano for his kind assistance with a number of our queries.
19. R.P. Polniaszek and S.E. Belmont, J. Org. Chem. 56, 4868 (1991).
20. R.P. Polniaszek and S.E Belmont, J. Org Chem. 55, 4688 (1990).
21. For other syntheses of indolizidine 167B, see ref. 4 and the following: C.W. Jefford, Q. Tang and A. Zaslona, J. Am. Chem. Soc. 113, 3513 (1991); E. Zeller, H. Sajus and D. Grierson, Synlett 44 (1991); A. Fleurant, J.P. Célérier and G. Lhommet, Tetrahedron: Asymmetry 3, 695 (1992); W.H. Pearson, R. Walavalkar, J.M. Schkeryantz, W.-K. Fang and J.D. Blickensdorf, J. Am. Chem. Soc. 115, 10183 (1993); C.W. Jefford and J.B. Wang, Tetrahedron Lett. 34, 3119 (1993); A. Fleurant, C. Saliou, J.P. Célérier, N. Platzer, T. V. Moc and G. Lhommet, J. Heterocyclic Chem. 32, 255 (1995); H. Takahata, H. Bandoh and T. Momose, Heterocycles 41, 1797 (1995); E. Lee, K.S. Li and J. Lim, Tetrahedron Lett. 37, 1445 (1996).
22. For other syntheses of indolizidine 167B, see ref. 4 and the following: C.W. Jefford, Q. Tang and A. Zaslona, J. Am. Chem. Soc. 113, 3513 (1991); E. Zeller, H. Sajus and D. Grierson, Synlett 44 (1991); A. Fleurant, J.P. Célérier and G. Lhommet, Tetrahedron: Asymmetry 3, 695 (1992); W.H. Pearson, R. Walavalkar, J.M. Schkeryantz, W.-K. Fang and J.D. Blickensdorf, J. Am. Chem. Soc. 115, 10183 (1993); C.W. Jefford and J.B. Wang, Tetrahedron Lett. 34, 3119 (1993); A. Fleurant, C. Saliou, J.P. Célérier, N. Platzer, T. V. Moc and G. Lhommet, J. Heterocyclic Chem. 32, 255 (1995); H. Takahata, H. Bandoh and T. Momose, Heterocycles 41, 1797 (1995); E. Lee, K.S. Li and J. Lim, Tetrahedron Lett. 37, 1445 (1996).
23. For other syntheses of indolizidine 167B, see ref. 4 and the following: C.W. Jefford, Q. Tang and A. Zaslona, J. Am. Chem. Soc. 113, 3513 (1991); E. Zeller, H. Sajus and D. Grierson, Synlett 44 (1991); A. Fleurant, J.P. Célérier and G. Lhommet, Tetrahedron: Asymmetry 3, 695 (1992); W.H. Pearson, R. Walavalkar, J.M. Schkeryantz, W.-K. Fang and J.D. Blickensdorf, J. Am. Chem. Soc. 115, 10183 (1993); C.W. Jefford and J.B. Wang, Tetrahedron Lett. 34, 3119 (1993); A. Fleurant, C. Saliou, J.P. Célérier, N. Platzer, T. V. Moc and G. Lhommet, J. Heterocyclic Chem. 32, 255 (1995); H. Takahata, H. Bandoh and T. Momose, Heterocycles 41, 1797 (1995); E. Lee, K.S. Li and J. Lim, Tetrahedron Lett. 37, 1445 (1996).
24. For other syntheses of indolizidine 167B, see ref. 4 and the following: C.W. Jefford, Q. Tang and A. Zaslona, J. Am. Chem. Soc. 113, 3513 (1991); E. Zeller, H. Sajus and D. Grierson, Synlett 44 (1991); A. Fleurant, J.P. Célérier and G. Lhommet, Tetrahedron: Asymmetry 3, 695 (1992); W.H. Pearson, R. Walavalkar, J.M. Schkeryantz, W.-K. Fang and J.D. Blickensdorf, J. Am. Chem. Soc. 115, 10183 (1993); C.W. Jefford and J.B. Wang, Tetrahedron Lett. 34, 3119 (1993); A. Fleurant, C. Saliou, J.P. Célérier, N. Platzer, T. V. Moc and G. Lhommet, J. Heterocyclic Chem. 32, 255 (1995); H. Takahata, H. Bandoh and T. Momose, Heterocycles 41, 1797 (1995); E. Lee, K.S. Li and J. Lim, Tetrahedron Lett. 37, 1445 (1996).
25. For other syntheses of indolizidine 167B, see ref. 4 and the following: C.W. Jefford, Q. Tang and A. Zaslona, J. Am. Chem. Soc. 113, 3513 (1991); E. Zeller, H. Sajus and D. Grierson, Synlett 44 (1991); A. Fleurant, J.P. Célérier and G. Lhommet, Tetrahedron: Asymmetry 3, 695 (1992); W.H. Pearson, R. Walavalkar, J.M. Schkeryantz, W.-K. Fang and J.D. Blickensdorf, J. Am. Chem. Soc. 115, 10183 (1993); C.W. Jefford and J.B. Wang, Tetrahedron Lett. 34, 3119 (1993); A. Fleurant, C. Saliou, J.P. Célérier, N. Platzer, T. V. Moc and G. Lhommet, J. Heterocyclic Chem. 32, 255 (1995); H. Takahata, H. Bandoh and T. Momose, Heterocycles 41, 1797 (1995); E. Lee, K.S. Li and J. Lim, Tetrahedron Lett. 37, 1445 (1996).
26. For other syntheses of indolizidine 167B, see ref. 4 and the following: C.W. Jefford, Q. Tang and A. Zaslona, J. Am. Chem. Soc. 113, 3513 (1991); E. Zeller, H. Sajus and D. Grierson, Synlett 44 (1991); A. Fleurant, J.P. Célérier and G. Lhommet, Tetrahedron: Asymmetry 3, 695 (1992); W.H. Pearson, R. Walavalkar, J.M. Schkeryantz, W.-K. Fang and J.D. Blickensdorf, J. Am. Chem. Soc. 115, 10183 (1993); C.W. Jefford and J.B. Wang, Tetrahedron Lett. 34, 3119 (1993); A. Fleurant, C. Saliou, J.P. Célérier, N. Platzer, T. V. Moc and G. Lhommet, J. Heterocyclic Chem. 32, 255 (1995); H. Takahata, H. Bandoh and T. Momose, Heterocycles 41, 1797 (1995); E. Lee, K.S. Li and J. Lim, Tetrahedron Lett. 37, 1445 (1996).
27. For other syntheses of indolizidine 167B, see ref. 4 and the following: C.W. Jefford, Q. Tang and A. Zaslona, J. Am. Chem. Soc. 113, 3513 (1991); E. Zeller, H. Sajus and D. Grierson, Synlett 44 (1991); A. Fleurant, J.P. Célérier and G. Lhommet, Tetrahedron: Asymmetry 3, 695 (1992); W.H. Pearson, R. Walavalkar, J.M. Schkeryantz, W.-K. Fang and J.D. Blickensdorf, J. Am. Chem. Soc. 115, 10183 (1993); C.W. Jefford and J.B. Wang, Tetrahedron Lett. 34, 3119 (1993); A. Fleurant, C. Saliou, J.P. Célérier, N. Platzer, T. V. Moc and G. Lhommet, J. Heterocyclic Chem. 32, 255 (1995); H. Takahata, H. Bandoh and T. Momose, Heterocycles 41, 1797 (1995); E. Lee, K.S. Li and J. Lim, Tetrahedron Lett. 37, 1445 (1996).
28. For other syntheses of indolizidine 167B, see ref. 4 and the following: C.W. Jefford, Q. Tang and A. Zaslona, J. Am. Chem. Soc. 113, 3513 (1991); E. Zeller, H. Sajus and D. Grierson, Synlett 44 (1991); A. Fleurant, J.P. Célérier and G. Lhommet, Tetrahedron: Asymmetry 3, 695 (1992); W.H. Pearson, R. Walavalkar, J.M. Schkeryantz, W.-K. Fang and J.D. Blickensdorf, J. Am. Chem. Soc. 115, 10183 (1993); C.W. Jefford and J.B. Wang, Tetrahedron Lett. 34, 3119 (1993); A. Fleurant, C. Saliou, J.P. Célérier, N. Platzer, T. V. Moc and G. Lhommet, J. Heterocyclic Chem. 32, 255 (1995); H. Takahata, H. Bandoh and T. Momose, Heterocycles 41, 1797 (1995); E. Lee, K.S. Li and J. Lim, Tetrahedron Lett. 37, 1445 (1996).
29. D.C. Cole, Tetrahedron 50, 9517 (1994).
30. S.G. Davies and O. Ichihara, Tetrahedron: Asymmetry 2, 183 (1991).
31. J.F. Costello, S.G. Davies and O. Ichihara, Tetrahedron: Asymmetry 5, 1999 (1994).
32. M.E. Bunnage, A.J. Burke, S.G. Davies and C.J. Goodwin, Tetrahedron: Asymmetry 6, 165 (1995).
33. J.C.A. Boeyens and C.F. Broli, unpublished results, University of the Witwatersrand (1995).