A tandem radical macrocyclisation-transannular cyclisation approach towards the taxanes

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 19, 1998, Pages 3181-3206

  Hitchcock, Stephen A ^a   Houldsworth, Stephen J ^a   Pattenden, Gerald ^a   Pryde, David C ^a   Thomson, Nicholas M ^a   Blake, Alexander J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749083656     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805268i     Document Type: Article

References (64)

1. (a) E. F. Rowinsky, L. A. Cazenave and R. C. Donehower, J. Natl. Cancer Inst., 1990, 82, 1247;
2. (b) E. K. Rowinsky and R. C. Donehower, Pharmacol. Ther., 1991, 52, 35;
3. (c) P. B. Schiff, J. Fant and S. B. Horwitz, Nature, 1979, 22, 665;
4. (d) J. J. Manfredi and S. B. Horwitz, Pharmacol. Ther., 1984, 25, 83.
5. For reviews see: C. S. Swindell, Org. Prep. Proced. Int., 1992, 23, 465;
6. K. C. Nicolaou, W.-M. Dai and R. K. Guy, Angew. Chem., Int. Ed. Engl., 1994, 33, 15;
7. A. N. Boa, P. R. Jenkins and N. J. Lawrence, Contemp. Org. Synth., 1994, 1, 47.
8. For recent developments see, for example: Y.-F. Lu and A. G. Fallis, Can. J. Chem., 1995, 73, 2239;
9. R. Hara, T. Furukawa, Y. Horiguchi and I. Kuwajima, J. Am. Chem. Soc., 1996, 118, 9186;
10. P. Magnus, L. Diorazio, T. J. Donohoe, M. Giles, P. Pye, J. Tarrant and S. Thom, Tetrahedron, 1996, 52, 14 147;
11. S. F. Martin, J.-M. Assercq, R. E. Austin, A. P. Dantanarayana, J. R. Fishpaugh, C. Gluchowski, D. E. Guinn, M. Hartmann, T. Tanaka, R. Wagner and J. B. White, Tetrahedron, 1995, 51, 3455;
12. L. A. Paquette, F. J. Montgomery and T.-Z. Wang, J. Org. Chem., 1995, 60, 7857;
13. C. S. Swindell and W. Fan, J. Org. Chem., 1996, 61, 1109;
14. J. D. Winkler, J. M. Holland and D. A. Peters, J. Org. Chem., 1996, 61, 9074; and references cited therein.
15. (a) C. S. Swindell, Org. Prep. Proced. Int., 1992, 23, 465;
16. (b) K. C. Nicolaou, W.-M. Dai and R. K. Guy, Angew. Chem., Int. Ed. Engl., 1994, 33, 15;
17. (c) A. N. Boa, P. R. Jenkins and N. J. Lawrence, Contemp. Org. Synth., 1994, 1, 47.
18. (a) R. A. Holton, C. Somoza, H.-B. Kim, F. Liang, R. J. Biediger, P. D. Boatman, M. Shindo, C. C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K. K. Murthi, L. N. Gentile and J. H. Liu, J. Am. Chem. Soc., 1994, 116, 1597;
19. R. A. Holton, C. Somoza, H.-B. Kim, F. Liang, R. J. Biediger, P. D. Boatman, M. Shindo, C. C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, K. K. Murthi, L. N. Gentile and J. H. Liu, J. Am. Chem. Soc., 1994, 116, 1599;
20. (b) K. C. Nicolaou, Z. Yang, J. J. Liu, H. Ueno, P. G. Nantermet, R. K. Guy, C. F. Claiborne, J. Renaud, E. A. Couladouros, K. Paulvannan and E. J. Sorensen, Nature, 1994, 367, 630;
21. K. C. Nicolaou, P. G. Nantermet, H. Ueno, R. K. Guy, E. A. Couladouros and E. J. Sorensen, J. Am. Chem. Soc., 1995, 117, 624;
22. K. C. Nicolaou, J.-J. Liu, Z. Yang, H. Ueno, E. J. Sorensen, C. F. Claiborne, R. K. Guy, C.-K. Hwang, M. Nakada and P. G. Nantermet, J. Am. Chem. Soc., 1995, 117, 634;
23. K. C. Nicolaou, Z. Yang, J.-J. Liu, P. G. Nantermet, C. F. Claibourne, J. Renaud, R. K. Guy and K. Shibayama, J. Am. Chem. Soc., 1995, 117, 645;
24. (c) J. J. Masters, J. T. Link, L. B. Snyder, W. B. Young and S. J. Danishefsky, Angew. Chem., Int. Ed. Engl., 1995, 34, 1723;
25. S. J. Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V. Magee, D. K. Jung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A. Coburn and M. J. Di Grandi, J. Am. Chem. Soc., 1996 118, 2843;
26. (d) P. A. Wender, N. F. Badham, S. P. Conway, P. E. Floreancig, T. E. Glass, J. B. Houze, N. E. Krauss, D. Lee, D. G. Marquess, P. L. McGrane, W. Meng, M. G. Natchus, A. J. Shuker, J. C. Sutton and R.E. Taylor, J. Am. Chem. Soc., 1997, 119, 2757.
27. (a) G. Pattenden, A. J. Smithies and D. S. Walter, Tetrahedron Lett., 1994, 35, 2413;
28. (b) G. Pattenden, A. J. Smithies, D. Tapolczay and D. S. Walter, J. Chem. Soc., Perkin Trans. 1, 1996, 7;
29. (c) M. J. Begley, G. Pattenden, A. J. Smithies and D. S. Walter, Tetrahedron Lett., 1994, 35, 2417;
30. (d) M. J. Begley, G. Pattenden, A. J. Smithies, D. Tapolczay and D. S. Walter, J. Chem. Soc., Perkin Trans. 1, 1996, 21;
31. (e) A. J. Blake, G. J. Hollingworth and G. Pattenden, Synlett, 1996, 643;
32. (f) G. Pattenden and P. Wiedenau, Tetrahedron Lett., 1997, 38, 3647.
33. S. Handa and G. Pattenden, Contemp. Org. Synth., 1997, 4, 196.
34. S. A. Hitchcock and G. Pattenden, Tetrahedron Lett., 1992, 33, 4843.
35. Preliminary communication: S. J. Houldsworth, G. Pattenden, D. C. Pryde and N. M. Thomson, J. Chem. Soc., Perkin Trans. 1, 1997, 1091.
36. P. S. Skell and A. Y. Garner, J. Am. Chem. Soc., 1956, 78, 5430;
37. S. R. Sandler, J. Org. Chem., 1967, 32, 3876.
38. S. V. Ley, J. Norman, W. P. Griffith and S. P. Marsden, Synthesis, 1994, 639.
39. The vinyl stannane 16 was prepared in two steps from pent-4-yn-1-ol; see A. J. Lensink and H. A. Budding, J. Organomet. Chem., 1968, 11, 533.
40. H. Firouzabadi and E. Ghaderi, Tetrahedron Lett., 1978, 839.
41. S. J. Houldsworth, PhD Thesis, University of Nottingham, 1995.
42. C. S. Swindell and B. P. Patel, Tetrahedron Lett., 1987, 28, 5275.
43. R. V. Bonnert and P. R. Jenkins, J. Chem. Soc., Perkin Trans. 1, 1989, 413.
44. We thank Professor D. P. Curran (Pittsburgh) for some earlier discussions and correspondence on this subject.
45. For example see: D. P. Curran and D. M. Rackiewicz, J. Am. Chem. Soc., 1985, 107, 1448;
46. J.-K. Choi and D. J. Hart, Tetrahedron, 1985, 41, 3959;
47. G. Stork and R. Mook, J. Am. Chem. Soc., 1987, 109, 2829;
48. D. L. Boger and R. J. Mathvink, J. Org. Chem., 1990, 55, 5442;
49. for later work see: D. Crich and D. Batty, J. Chem. Soc., Perkin Trans. 1, 1992, 3193;
50. R. A. Batey, J. D. Harling and W. B. Motherwell, Tetrahedron, 1996, 52, 11 421;
51. J. E. Baldwin, R. M. Adlington and S. H. Ramcharitar, Tetrahedron, 1992, 48, 3413;
52. A. J. Blake, G. J. Hollingworth and G. Pattenden, Synlett, 1996, 643.
53. See: N. M. Thomson, PhD Thesis, University of Nottingham, 1997.
54. For example see: W. R. Leonard and T. Livinghouse, Tetrahedron Lett., 1985, 26, 6431;
55. K. K. Wang, Z. Wang, A. Tarli and P. Gannet, J. Am. Chem. Soc., 1996, 118, 10 783;
56. D. P. Curran and J. Xu, J. Am. Chem. Soc., 1996, 118, 3142.
57. R. Amouroux, M. Jatczak and M. Chastrette, Bull. Soc. Chim. Fr., 1987, 505.
58. (a) D. B. Dess and J. C. Martin, J. Org. Chem., 1983, 48, 4165;
59. (b) D. B. Dess and J. C. Martin, J. Am. Chem. Soc., 1991, 113, 7277.
60. L. Alkonyi and D. Szabo, Chem. Ber., 1967, 100, 2273.
61. G. M. Sheldrick, SHELXS-86; Acta Crystallogr., Sect. A, 1990, 46, 467.
62. G. M. Sheldrick, SHELXL-93, University of Göttingen, Germany, 1993.
63. G. M. Sheldrick, SHELXTL/PC ver. 5.03. Siemens Analytical Instruments Inc., Madison, WI, 1994.
64. S. R. Sandler, J. Org. Chem., 1967, 32, 3876.