A novel total synthesis of (±)-aspidospermidine

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 8, 1999, Pages 995-1001

  Callaghan, Owen ^a   Lampard, Christopher ^a   Kennedy, Alan R ^a   Murphy, John A ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001149012     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900335e     Document Type: Article

References (49)

1. Previous syntheses of aspidospermidine: (a) A. Camerman, N. Camerman, J. P. Kutney, E. Piers and J. Trotter, Tetrahedron Lett., 1965, 637;
2. (b) 3. Harley-Mason and M. Kaplan, J. Chem. Soc., Client. Commun., 1967, 915;
3. J.-Y. Laronze, J. Laronze-Fontaine, J. Levy, and J. LeMen, Tetrahedron Lett., 1974, 491;
4. T. Gallagher, P. Magnus and J. C. Huffman, J. Am. Chem. Soc., 1983, 105, 4750;
5. Y. Ban, K. Yoshida, J. Goto, T. Oishi and E. Takeda, Tetrahedron, 1983, 39, 3657;
6. (/) M. Node, H. Nagasawa and K. Fuji, J. Am. Chem. Soc., 1987, 109, 7901;
7. (g) S. B. Mandai, V. S. Giri, M. S. Sabeena and S. C. Pakrashi, J. Org. Chem., 1988, 53, 4236;
8. (A) P. Le Menez, N. Kunesch, S. Liu and E. Wenkert, J. Org. Chem., 1991, 56, 2915;
9. (/) E. Wenkert and S. Liu, J. Org. Chem., 1994, 59, 7677;
10. (J) D. Desmaële and J. d'Angelo, J. Org. Chem., 1994, 59, 2292;
11. (Ar) P. Forns, A. Diaz and M. Rubiralta, J. Org. Chem., 1996, 61, 7882;
12. (/) A. G. Schultz and L. Pettus, J. Org. Chem., 1997, 62, 6855.
13. For synthesis of A'-benzylaspidospermidine, see: N. BenchekrounMounir, D. Dugat, J.-C. Gramain and H.-P. Husson, J. Org. Chem., 1993, 58, 6457.
14. For a tandem radical approach to the Aspidosperma skeleton, see P. J. Parsons, C. S. Penkert, M. C. Cramp, R. I. West, J. Warrington and M. C. Saraiva, Synletl, 1995, 507.
15. Syntheses of vinblastine: P. Potier, N. Langlois, Y. Langlois and F. Guéritte, J. Chem. Soc., Chem. Commun., 1975, 670;
16. J. Am. Chem. Soc., 1976, 98, 7017;
17. J. P. Kutney, A. H. Ratcliffe, A. M. Treasurywalla 'and S. Wunderly, lleterocycles, 1975, 3, 639;
18. G. Schill, C. U. Priester, U. F. Windhocvel and H. Fritz, Tetrahedron, 1987, 43, 3765;
19. J. Vucovic, A. E. Goodbody, J. P. Kutney and M. Misawa, Tetrahedron, 1988, 44, 325;
20. P. Magnus, A. Stamford and M. Ladlow, J. Am. Cliem. Soc., 1990, 112, 8210;
21. M. E. Kuehne, P. A. Maison and W. G. Bornmann, J. Org. Chcm., 1991, 56, 513;
22. R. J. Sundberg, J.-L. Bettiol, K. G. Gadamasetti, M. Marshalla and L. Kelsh, Bioorg. Med. Chem. Lett., 1994, 4, 1999;
23. I. Tabakovic, E. Gunic and I. Juranic, J. Org. Chem., 1997, 62, 947.
24. S. Lobert, B. Vulevic and J. J. Correia, Biochemistry, 1996, 35, 6806;
25. S. S. Rai and J. WolfT, J. Bio!. Chem., 1996, 271, 14707;
26. V. Prakash and S. N. Timasheff, Biochemistry, 1991, 30, 873;
27. L. S. Borman, M. E. Kuehne, P. A. Maison, I. Marko and T. C. Zebovilz, J. Biol. Chem., 1988, 263, 6945;
28. A. R. Safa, E. Hamel and R. L. Felsled, Biochemistry, 1987, 26, 97.
29. P. Polier, Semin. Oncol., 1989, 16, 2.
30. D. L. J. Clive, Y. Tao, A. Khodabocus, Y.-J. Wu, A. G. Angoh, S. M. Benne, C. N. Boddy, L. Bordeleau, D. Kellner, G. Kleiner, D. S. Middleton, C. J. Nichols, S. R. Richardson and P. G. Vernon, J. Am. Chem. Soc, , 1994, 1\6; 11275.
31. D. L. J. Clive, H. W. Manning and T. L. B. Boivin, J. Chem. Soc., Chem. Commun., 1990, 972.
32. A. L. J. Beckwith and G. F. Meijs, J. Org. Chem., 1987, 52, 1922;
33. A. N. Abeywickrema and A. L. J. Beckwith, J. Org. Chem., 1987, 52, 2568.
34. C. Lampard, J. A. Murphy and N. Lewis, J. Chem. Soc., Chem. Commun., 1993, 295;
35. R. J. Fletcher, C. Lampard, J. A. Murphy and N. Lewis, / Chem. Soc., Perkin Trans. I, 1995, 623.
36. R. Flelcher, M. Kizil, C. Lampard, J. A. Murphy and S. J. Roome, J. Chem. Soc., Perkin Trans. J, 1998, 2341.
37. K. Narasaka, K. Soai and T. Mukaiyama, Chcm Lett., 1974, 1223;
38. T. Yanami, M. Miyashita and A. Yoshikoshi, J. Org. Chem., 1980, 45, 607.
39. Semi-empirical molecular modelling studies were performed at the AMI level using Spartan 4.1, produced by Wavefunction Inc., Irvine, CA92715.
40. (a) For related studies, see: A. Azzouzi, B. Perrin, M.-E. Sinibaldi, J.-C. Gramain and C. Lavaud, Tetrahedron Lett., 1993, 34, 5451;
41. A. Azzouzi, B. Perrin, M. E. Sinibaldi, D. Gardette, C. Lavaud, D. Vallee-Goyet, J.-C. Gramain and A. Kerbal, Bull. Soc. Cliim. Fr., 1995, 132, 681.
42. E. Piers and J. Renaud, J. Org. Chem., 1993, 58, 11.
43. M. E. Kuehne, T. Wang and P. J. Sealon, J. Org. Chem., 1996, 61, 6001.
44. O. Callaghan, C. Lampard, A. R. Kennedy and J. A. Murphy, Tetrahedron Lett., 1999, 40, 161.
45. Enanliomerically pure aspidospermidine should be accessible by this route using a single enantiomer of 2-allylcylohex-2-en-l-ol, the ultimate source of this chiral centre (rather than the racemic compound used here). This compound has been prepared (réf. 19) in >96% ee and Mitsunobu reactions on cyclohex-2-enols have been found to proceed with clean inversion (réf. 20) of stereochemistry.
46. C. Y. Hong, N. Kado and L. E. Overman, J. Am. Chem. Soc., 1993, 115, 11028.
47. K. A. Parker and D. Fokas, J. Am. Chem. Soc., 1993, 114, 9688;
48. J. Org. Chem., 1994, 59, 3933.
49. TeXsan, Version 1.6, Crystal Structure Analysis Package, Molecular Structure Corporation, The Woodlands, Texas 77381, 1992.