Highly stereoselective trans addition of π-type nucleophiles to a bicyclic N-acyliminium ion - Application to the synthesis of indolizidine and pyrrolizidine alkaloids

European Journal of Organic Chemistry

Volumn , Issue 9, 1998, Pages 1955-1963

  Dhimane, Hamid ^a   Vanucci Bacqué, Corinne ^a   Hamon, Louis ^a   Lhommet, Gérard ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Indolizidine; N acyliminium; Pyrrolidine; Pyrrolizidine; Stereoselective

Indexed keywords

EID: 0002543115     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199809)1998:9<1955::AID-EJOC1955>3.0.CO;2-U     Document Type: Article

References (43)

1. A. R. Mattock, in Chemistry and Toxycology of Pyrrolidine Alkaloids, Academic Press, London, 1986.
2. T. Tokuyama, N. Nishimori, I. L. Karle, M. W. Edwards, J. W. Daly, Tetrahedron 1986, 42, 3453-3460.
3. [3a] T. Katsuki, M. Yamasuchi, J. Syn. Org. Chem. Jpn. 1986, 44, 532-544.
4. [3b] L.-Y. Chen, L. Ghosez, Tetrahedron Lett. 1990, 31, 4467-4470.
5. [3c] K. Fugi, M. Node, Y. Naniwa, T. Kawabata, Tetrahedron Lett. 1990, 31, 3175-3178.
6. [3d] J. K. Whitesell, Chem. Rev. 1989, 89, 1581-1590 and references cited herein.
7. [3e] S. Ikegami, H. Uchiyama, T. Hayama, T. Katsuki, M. Yamagushi, Tetrahedron 1988, 44, 5333-5342.
8. [4a] P. Q Huang, S. Arseniyadis, H. P. Husson, Tetrahedron Lett. 1987, 28, 547-550.
9. [4b] H. Takahata, H. Takehara, N. Ohkubo, T. Momose, Tetrahedron: Asymmetry 1990, 1, 561-566.
10. [4c] M. Skrinjar, L. G. Wistrand, Tetrahedron Lett. 1990, 31, 1775-1778.
11. [4d] S. Rosset, J.-P. Célérier, G. Lhommet, Tetrahedon Lett. 1991, 32, 7521-7526.
12. [4e] G. Vo Thanh, J.-P. Célérier, G. Lhommet, Tetrahedron: Asymmetry 1996, 7, 2211-2212.
13. [4f] G. Vo Thanh, J.-P. Célérier, A. Fleurant, C. Grandjean, S. Rosset, G. Lhommet, Heterocycles 1996, 43, 1381-1384.
14. L. G. Wistrand, M. Skrinjar, Tetrahedron 1991, 47, 573-582.
15. C. Célimène, H. Dhimane, G. Lhommet, Tetrahedron, in press.
16. T. Shono, T. Fujita, Y. Matsumura, Chem. Lett. 1991, 81, 80-84.
17. H. Dhimane, C. Vanucci, G. Lhommet, Tetrahedron Lett. 1997, 38, 1415-1418.
18. [9a] Y. Imada, M. Yasushi, Y. Mitsue, K. Ike, K. Washizuta, Bull. Chem. Soc. Jpn. 1996, 69, 2079-2090.
19. [9b] W. Wiegrebe, E.-G. Herrmann, U. P. Schlunegger, H. Budzikiewicz, Helv. Chem. Acta 1974, 57, 301-314.
20. S.-I. Murahashi, T. Naota, N. Miyaguchi, T. Nakato, Tetrahedron Lett. 1992, 33, 6991-6994.
21. T. Shono, Tetrahedron 1984, 40, 811-850.
22. F. Driessens, C. Hootele, Can J. Chem. 1991, 69, 211-217.
23. S.-B. Huang, J. S. Nelson, D. D. Weller, J. Org Chem. 1991, 56, 6007-6018.
24. C. Pedregal, J. Ezquerra, A. Escribano, M. C. Carreno, J. L. Garcia Ruano, Tetrahedron Lett. 1994, 35, 2053-2056.
25. [8]
26. C. Agami, F. Couty, L. Hamon, O. Venier, Tetrahedron Lett. 1994, 34, 4509-4512.
27. 3, PPTS, MeOH] followed by cyclisation, resulted in a poor overall yield of 1a (25%).
28. 2Me), followed by a three-step procedure leading to the required bicyclic oxazolidmone.
29. A. G. M. Barrett, D. Pilipauska, J Org. Chem. 1991, 56, 2787-2800.
30. The geometries of the initial states were optimised by using the Davidson-Fletcher-Powell algorithm (FLEPO procedure), minimising the energy with respect to all internal coordinates. Approximate transition states were obtained from the energy profiles in a reaction path (the reaction coordinates being the distance between the carbon atom of C=N and the reactive terminal carbon atom of the allylsilane), then the transition states were optimised by minimising the energy gradient (NLLSQ procedure).
31. M. J. Dewar, E. G. Zoebisch, E. F. Herly, J. J. P. Stewart, J. Amer. Chem. Soc: 1985, 107, 3902-3909: AMPAC version 2.14.
32. A. Fleurant, J.-C. Célérier, G. Lhommet. Tetrahedron: Asymmetry 1993, 4, 1429-1430.
33. J. W. Daly, J. Nat. Prod. 1998, 61, 162-172.
34. [24a] T. H. Jones, M. S. Blum, J Org. Chem. 1980, 45, 4778-4780
35. [24b] T. H. Jones, S. M. Stahly, A. W. Don, M. S. Blum, J Chem. Ecol. 1988, 14, 2197.
36. [24c] The optical rotation of naturally occuring sample of xenovenine has not been determined so far because of its scarcity.
37. O. Provost, J.-P. Célérier, H. Petit, G. Lhommet, J. Org Chem. 1992, 57, 2163-2166.
38. W. Oppolzer, C. G. Bochet, E. Merifield, Tetrahedron Lett. 1994, 35, 7015-7018.
39. H. Takahata, H. Bandoh, T. Momose, J. Org. Chem. 1992, 57, 4401-4404.
40. Compound 1a was equally prepared by refluxing 5 in MeOH in 39% yield. The spectral data of 1'a were deduced by difference with those of 1a.
41. G. M Sheldrick, SHELXS86, Program for the solution of crystal structures. University of Göttingen. Federal Republic of Germany, 1986.
42. D. J Watkin, C. K Prout, R. J Carruthers, P. W Betteridge, CRYSTALS. Issue 10, Chemical Crystallography Laboratory, Oxford, UK. 1996.
43. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no CCDC-101210. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ. UK [fax: int. code + 44-(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk].