Vinylogous urethanes in alkaloid synthesis. Applications to the synthesis of racemic indolizidine 209B and its (5A*,8S*,8aS*)-(±) diastereomer, and to (-)-indolizidine 209B

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 12, 2000, Pages 1919-1928

  Michael, Joseph P ^a   Gravestock, David ^a  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

STEREOSELECTIVE REDUCTIONS;

AROMATIC COMPOUNDS;

EID: 0034697704     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001853h     Document Type: Article

References (45)

1. J. W. Daly, H. M. Garraffb and T. F. Spande, in The Alkaloids (N. Y.), ed. G. A. Cordell, Academic Press, San Diego, 1993, vol. 43, pp. 185-288.
2. J. W. Daly, H. M. Garraffb and T. F. Spande, in Alkaloids: Chemical and Biological Perspectives, ed. S. W. Pelletier, Pergamon Press, Amsterdam, 1999, vol. 13, pp. 1-161.
3. J. W. Daly, in The Alkaloids (N. Y.), ed. G. A. Cordell, Academic Press, San Diego, 1998, vol. 50, pp. 141-169.
4. T. H. Joncs, J. S. T. Gorman, R. R. Sneliing, J. H. C. Delabie, M. S. Blum, H. M. Garraffo, P. Jain, J. W. Daly and T. F. Spande, J. Chem. Ecol., 1999, 25, 1179.
5. J. P. Michael, Nat. Prod Rep., 1999, 16, 675.
6. J. W. Daly, Y. Nishizawa, W. L. Padgett, T. Tokuyama, A. L. Smith, A. B. Holmes. C. Kibayashi and R. S. Aronstam, Neurochem. Res., 1991, 16, 1213.
7. J. P. Michael, C. B. de Koning, D. Gravestock, G. D. Hosken, A. S. Howard, C. M. Jungmann, R. W. M. Krause, A. S. Parsons, S. C. Pelly and T. V. Stanbury, Pure Appl. Cliem., 1999, 71, 979.
8. J. P. Michael and D. Gravestock, Eur. J. Org. Chem., 1998, 865.
9. J. P. Michael and D. Gravestock, 5. Afr. J. Chem., 1998, 51, 146.
10. J. W. Daly, C. W. Myers and N. Whittaker, Toxicon, 1987, 25, 1023.
11. J. P. Michael and D. Gravestock, Synlett, 1996, 981.
12. J. P. Michael and D. Gravestock, Pure Appl. Chem., 1997, 69, 583.
13. For syntheses of indolizine 209B published before 1996, see ref. 11. For subsequently published total or formal syntheses, see the following: (a) N. Toyooka, K.- Tanaka, T. Momose, J. W. Daly and H. M. Garraflb, Tetrahedron, 1997, 53, 9553;
14. (b) A. Bardou, J.-P. Celerier and G. Lhommet, Tetrahedron Lett., 1998, 39, 5189.
15. D. Brillon, Syhth. Commun., 1990, 20, 3085.
16. (a) R. S. Marmor, J. Org. Chem., 1972, 37, 2901;
17. (b) I. Fleming and J. M. Mwaniki, J. Chem: Soc., Perkin Trans. 1, 1998, 1237.
18. M: Roth, P. Dubs, E. Götschi and A. Eschenmoser, Helv. Chim. Acta, 1971, 54, 710.
19. K. Shiosaki, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon Press, Oxford, 1991, vol. 2, pp. 865-892.
20. R. V. Stevens, Acc. Chem. Res., 1984, 17, 289.
21. F. Bohlmann, Chem. Ber., 1985, 91, 2157.
22. R. P. Polniaszek and S. E. Belmont, J. Org. Chem., 1991, 56, 4868.
23. A. B. Holmes, A. L. Smith, S. F. Williams, L. R. Hughes, Z. Lidert and C. Swithenbank, J. Org. Chem., 1991, 56, 1393.
24. C. W. Jefford, K. Sienkiewicz and S. R. Thornton, Helv. Chim. Acta, 1995, 78, 1511.
25. L. W. Covert and H. Adkins, J. Am. Chem. Soc., 1932, 54, 4116.
26. See, for example, (a) G. W. Kenner and M. A. Murray, J. Chem. Soc., 1949, S178;
27. (b) J. Nieuwenhuis and J. F. Arens, Reel. Trar. Chim. Pays-Bas, 1958, 77, 1153;
28. E. Caspi, E. Cullen and P. K. Graver, J. Chem. Sor., 1963, 212.
29. R. G. F. Giles, I. R. Green, L. S. Knight, V. R. Lee Son and S. C. Yorke, J. Chem. Soc., Perkin Trans. 1, 1994, 859.
30. D. Gnecco, C. Marazano and B. C. Das, J. Chem. Soc., Chem. Commun., 1991, 625.
31. Y.-S. Wong, D. Gnecco, C. Marazano, A. Chiaroni, C. Riche, A. Billion and B. C. Das, Tetrahedron, 1998, 54, 9357.
32. D. C. Cole, Tetrahedron, 1994, 50, 9517.
33. G. Cardillo and C. Tomasini, Chem. Soc. Rer., 1996, 25, 117.
34. S. G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1991, 2, 183.
35. J. F. Costello, S. G. Davies and O. Ichihara, Tetrahedron: Asymmetry, 1994, 5, 1999.
36. G. F. Griffiths, G. W. Kenner, S. W. McCombie, K. M. Smith and M. J. Suttpn, Tetrahedron, 1976, 32, 275.
37. M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush and T. Sakai, Tetrahedron Lett., 1984, 25, 2183.
38. S. G. Davies and D. R. Fenwick, J. Chem. Soc., Chem. Commun., 1995, 1109.
39. M. E. Bunnage, A. J. Burke, S. G. Davies and C. J. Goodwin, Tetrahedron: Asymmetry, 1995, 6, 165.
40. J. C. A. Boeyens and C. F. Broli, unpublished results.
41. M. S. Manhas and S. J. Jeng, J. Org. Chem., 1967, 32, 1246.
42. P. H: Lambert, M. Vaultier and R. Carrie, J. Org. Chem., 1985, 50, 5352.
43. J. P. Michael, G. D. Hosken and A. S. Howard, Tetrahedron, 1988, 44, 3025.
44. P. J. Gareggand B. Samuelsson, J. Chem. Soc., Perkin Trans. 1, 1980, 2866.
45. H. M. Garraffo, P. Jain, T. F. Spande and J. W. Daly, J. Nat. Prod, 1997, 60, 2.