Tetrathiafulvalene-mediated stereoselective synthesis of the tetracyclic core of Aspidosperma alkaloids

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 15, 1998, Pages 2341-2351

  Fletcher, Rodney ^b   Kizil, Murat ^b   Lampard, Christopher ^a,b   Murphy, John A ^a,b   Roome, Stephen J ^b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748725566     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a802974a     Document Type: Article

References (33)

1. (a) J. A. Murphy, C. Lampard and N. Lewis, J. Chem. Soc., Chem. Commun., 1993, 295;
2. (b) J. A. Murphy, C. Lampard, F. Rasheed, N. Lewis, M. B. Hursthouse and D. E. Hibbs, Tetrahedron Lett., 1994, 35, 8675;
3. (c) J. A. Murphy, M. J. Begley and S. J. Roome, Tetrahedron Lett., 1994, 35, 8679;
4. (d) J. A. Murphy, R. J. Fletcher, C. Lampard and N. Lewis, J. Chem. Soc., Perkin Trans 1, 1995, 623;
5. (e) J. A. Murphy and S. J. Roome, J. Chem. Soc., Perkin Trans 1, 1995, 1349;
6. (f) J. A. Murphy and M. Kizil, J. Chem. Soc., Chem. Commun., 1995, 1409;
7. (g) J. A. Murphy, N. Lewis, F. Rasheed and S. J. Roome, Chem. Commun., 1996, 737;
8. (h) R. J. Fletcher, D. E. Hibbs, M. Hursthouse, C. Lampard, J. A. Murphy and S. J. Roome, Chem. Commun., 1996, 739;
9. (i) J. A. Murphy, F. Rasheed, S. Gastaldi, T. Ravishanker and N. Lewis, J. Chem. Soc., Perkin Trans 1, 1997, 1549;
10. (j) N. Bashir, O. Callaghan, J. A. Murphy, T. Ravishanker and S. J. Roome, Tetrahedron Lett., 1997, 38, 6255;
11. (k) O. Callaghan, X. Franck and J. A. Murphy, Chem. Commun., 1997, 1923;
12. (l) T. Koizumi, N. Bashir and J. A. Murphy, Tetrahedron Lett., 1997, 38, 7635.
13. N. Benchekroun-Mounir, D. Dugat, J.-C. Gramain and H.-P. Husson, J. Org. Chem., 1993, 58, 6457;
14. A. Azzouzi, B. Perrin, M.-E. Sinibaldi, J.-C. Gramain and C. Lavaud, Tetrahedron Lett., 1993, 34, 5451;
15. A. Azzouzi, B. Perrin, M. E. Sinibaldi, D. Gardette, C. Lavaud, D. Valleegoyet, J.-C. Gramain and A. Kerbal, Bull. Soc. Chim. Fr., 1995, 132, 681.
16. R. B. Woodward, M. Cava, NV. D. Ollis, A. Hunger, H. U. Daeniker and K. Schenker, J. Am. Chem. Soc., 1954, 76, 4749;
17. E. Wenkert, J. Am. Chem. Soc., 1962, 84, 98;
18. R. Thomas, Tetrahedron Lett., 1961, 544;
19. A. A. Qureshi and A. I. Scott, J. Chem. Soc., Chem. Commun., 1968, 945, 947, 948;
20. A. R. Battersby, J. C. Byrne, R. S. Kapil, J. A. Martin, T. G. Payne, D. Arigoni and P. Loew, J. Chem. Soc., Chem. Commun., 1968, 951.
21. P. Magnus, T. Gallagher, P. Brown and P. Pappalardo, Acc. Chem. Res., 1984, 17, 35;
22. P. Magnus, M. Giles, R. Bonnert, C. S. Kim, L. McQuire, A. Merritt and N. Vicker, J. Am. Chem. Soc., 1992, 114, 4403;
23. V. H. Rawal, C. Mihoud and R. F. Monestel, J. Am. Chem. Soc., 1993, 115, 3030;
24. S. R. Angle, J. M. Fevig, S. D. Knight, R. W. Marquis, Jr. and L. E. Overman, J. Am. Chem. Soc., 1993, 115, 3966;
25. S. D. Knight, L. E. Overman and G. Pairaudeau, J. Am. Chem. Soc., 1993, 115, 9293.
26. For a preliminary account of this work, see J. A. Murphy, M. Kizil and C. Lampard, Tetrahedron Lett., 1996, 37, 2511.
27. D. F. Taber, J. Org. Chem., 1976, 41, 2649;
28. D. F. Taber, B. P. Gunn and I. C. Chiu, Org. Synth., 1990, Coll. Vol. VII, 249.
29. C. Y. Hong, N. Kado and L. E. Overman, J. Am. Chem. Soc., 1993, 115, 11028.
30. K. A. Parker and D. Fokas, J. Am. Chem. Soc., 1992, 114, 9688;
31. J. Org. Chem., 1994, 59, 3933.
32. J. A. Murphy and M. Kizil, J. Chem. Soc., Chem. Commun., 1995, 1409.
33. M. Kizil, Ph.D. Thesis, University of Nottingham, 1997.