Total synthesis of baccatin III and taxol

Journal of the American Chemical Society

Volumn 118, Issue 12, 1996, Pages 2843-2859

  Danishefsky, Samuel J ^a,b   Masters, John J ^a,c   Young, Wendy B ^a,d   Link, J T ^a,b   Snyder, Lawrence B ^a,e   Magee, Thomas V ^a,f   Jung, David K ^a,g   Isaacs, Richard C A ^a,h   Bornmann, William G ^a   Alaimo, Cheryl A ^a,h   Coburn, Craig A ^a,h   Di Grandi, Martin J ^a,h  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Havemeyer Hall ^*  (United States)

^c ELI LILLY AND COMPANY   (United States)

^d Arris Pharmaceuticals   (United States)

^e BRISTOL MYERS SQUIBB   (United States)

^f PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^g GLAXOSMITHKLINE   (United States)

^h MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 11044223276     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952692a     Document Type: Article

References (65)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325.
2. Horwitz, S. B.; Fant, J.; Schiff, P. B. Nature 1979, 277, 665.
3. Mangatal, L.; Adeline, M. T., Guenard, D.; Gueritte-Voegelein, F.; Potier, P. Tetrahedron 1989, 45, 4177.
4. For reviews, see: (a) Georg, G. I.; Chen, T, T.; Ojima, I.; Vyas, D. M. Taxane Anticancer Agents; American Cancer Society: San Diego, 1995. (b) Kingston, D. G. I.; Molinero, A. A.; Rimoldo, J. M. Progress in the Chemistry of Organic Natural Products 61, Springer-Verlag: New York, 1993.
5. For reviews, see: (a) Georg, G. I.; Chen, T, T.; Ojima, I.; Vyas, D. M. Taxane Anticancer Agents; American Cancer Society: San Diego, 1995. (b) Kingston, D. G. I.; Molinero, A. A.; Rimoldo, J. M. Progress in the Chemistry of Organic Natural Products 61, Springer-Verlag: New York, 1993.
6. (a) Denis, J. N.; Greene, A. E.; Guenard, D.; Gueritte-Voegelein, F.; Mangatal, L.; Potier, P. J. Am. Chem. Soc. 1988, 110, 5917.
7. (b) Holton, R. A. Eur. Pat. Appl. EP400.971, 1990; Chem. Abstr. 1990, 114, 164568q.
8. (c) Holton, R. A. Workshop on Taxol and Taxus, 1991.
9. (d) Ojima, I.; Habus, I.; Zhao, M.; Georg. G. I ; Jayasinghe, L. R J. Org. Chem. 1991, 56, 1681.
10. (e) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M ; Park, Y. H.; Sun, C. M.; Brigaud, T. Tetrahedron 1992, 48, 6985.
11. (f) Ojima, I.; Sun, C. M.; Zucco, M.; Park, Y. M.; Duclos, O.; Kuduk, S. Tetrahedron Lett. 1993, 34, 4149.
12. For reviews, see: (a) Swindell, C. S. Studies in Natural Products Chemistry, Vol. 12; Elsevier Science Publishers: New York, 1993; pp 179-231. (b) Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15.
13. For reviews, see: (a) Swindell, C. S. Studies in Natural Products Chemistry, Vol. 12; Elsevier Science Publishers: New York, 1993; pp 179-231. (b) Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem., Int. Ed. Engl. 1994, 33, 15.
14. (a) Nicolaou, K. C.; Zang, Z., Liu, J. J.; Ueno, H.; Nantermet, P. G., Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E. J. Nature 1994, 367, 630.
15. (b) Nicolaou, K. C.; Nantermet, P. G., Ueno, H.; Guy, R. K.; Coulandouros, E. A.; Sorensen, E. J. J. Am. Chem Soc. 1995, 117, 624.
16. (c) Nicolaou, K. C.; Liu, J. J.; Yang, H ; Ueno, H.; Sorensen, E. J.; Claiborne, C. F.; Guy, R. K.; Hwang, C. K.; Nakada, M.; Nantermet, P. G. J. Am. Chem Soc. 1995, 117, 634.
17. (d) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Nantermet, P. G.; Claiborne, C. F.; Renaud, J.; Guy, R. K.; Shibayama, K. J. Am. Chem Soc: 1995, 117, 645.
18. (e) Nicolaou, K. C.; Ueno, H.; Liu, J. J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653.
19. (a) Holton, R. A.; Somoza, C.; Kim, H. B.; Liang, F.; Biediger, R. J., Boatman, D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. S.; Liu, J H. J. Am. Chem. Soc. 1994, 116, 1597.
20. (b) Holton, R. A.; Kim, H. B.; Somoza, C., Liang, F.; Biediger, R. J.; Boatman, D.; Shindo, M.; Smith, C. C ; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C ; Vu, P ; Tang, S ; Zhang, P.; Murthi, K. K.; Gentile, L. S., Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599
21. For a preliminary account of this work, see: Masters, J. J.; Link, J. T.; Snyder, L. B., Young, W. B and Danishefsky, S. J. Angew. Chem. 1995, 34, 1723.
22. (a) Wieland, P.; Miescher, K. Helv. Chim. Acta 1950, 33, 2215.
23. (b) Ramachandrin, S.; Newman, M. S. Organic Syntheses; Wiley; New York, 1973; Collect. Vol. V. p 486
24. (c) Hargreaves, J. H.; Hickmott, P. W., Hopkins, B. J. J. Chem. Soc. C 1968, 2599.
25. Kende, A. S.; Johnson, S., Sanfillipo, P.; Hodges, J. C.; Jungheim, L N. J. Am Chem. Soc. 1986, 108, 3513.
26. Harada, N.; Sugioka, T.; Hisashi, U: Kuriki, T. Synthesis 1990, 53 and references therein.
27. The R version of 5 is equally accessible and could be used to synthesize ent-baccatin III. We have, in fact, prepared late stage ent intermediates by this method.
28. The Chemistry and Pharmacology of Taxol: Farina, V., Ed.; Elsevier Press: New York, 1995.
29. Heathcock, C. H.; Ratcliffe, R. J. Am. Chem. Soc 1971, 93, 1746.
30. Magee, T V.; Bornmann, W. G.; Isaacs, R. C A.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 3274. This exploratory effort was conducted in the racemic series.
31. Corey, E J.; Chaykavsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
32. Waddell, T. G.; Ross, P. A. J. Org. Chem. 1987, 52, 4802.
33. Berkowitz, W. F.; Amarasekara, A. S.; Perumattam, J. J. J. Org. Chem. 1987, 52, 3745.
34. Isaacs, R. C. A.; Di Grandi, M. J.; Danishafsky, S. J. J. Org. Chem. 1993, 58, 3938.
35. Ettouate, L.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1991, 47, 9823.
36. Di Grandi, M. J.; Coburn, C. A.; Isaacs, R. C. A.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 7728.
37. Schreiber, S. L.; Claus, R. E.; Reagan, J. Tetrahedron Lett. 1982, 23, 3867.
38. (a) Wharton, P. S.; Bohlen, D. H. J. Org. Chem. 1961, 26, 3615.
39. (b) Maas, D. D.; Blagg, M.; Wiemer, D. F. J. Org. Chem. 1984, 49, 853.
40. Di Grandi, M. J.; Jung, D. K.; Krol, W. J.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 4989.
41. (a) Rubottom, G. M.; Vazquez, M. A.; Pelegrina, D. R. Tetrahedron Lett. 1972, 3375.
42. (b) Grieco, P. A.; Gilman, S.; Nishizawa, M J. Org. Chem. 1976, 41, 1485.
43. For two examples describing the reduction of this scheme to practice, albeit in much simpler (ring C aromatic) settings, see: (a) Swindell, C. S.; Chander, M. C.; Heerding, P. G.; Rahman, L. T.; Raman, V.; Venkataraman, H. Tetrahedron Lett. 1993, 34, 7005. (b) Swindell C. S.; Fan, W. and Klimko, P. G. Tetrahedron Lett. 1994, 35, 4959.
44. For two examples describing the reduction of this scheme to practice, albeit in much simpler (ring C aromatic) settings, see: (a) Swindell, C. S.; Chander, M. C.; Heerding, P. G.; Rahman, L. T.; Raman, V.; Venkataraman, H. Tetrahedron Lett. 1993, 34, 7005. (b) Swindell C. S.; Fan, W. and Klimko, P. G. Tetrahedron Lett. 1994, 35, 4959.
45. Masters, I. J ; Jung, D. K.; Danishefsky, S. J.; Snyder, L. B.; Park, T. K.; Isaacs, R. C. A.; Alaimo, C. A.; Young, W. B. Angew. Chem. Int. Ed. Engl. 1995, 34, 452.
46. Barton, D. H. R.; Bashiardes, G.; Fourrey. J.-L. Tetrahedron 1988, 44, 147-162.
47. For a review, see: Blomberg and Hartog. Synthesis 1977, 18-30.
48. Kress, M. H., Ruel, R ; Miller, W H.; Kishi, Y. Tetrahedron Lett. 1993, 34, 5999-6003.
49. Heck, R. F. Palladium Reagents in Organic Syntheses: Academic Press: New York, 1985; p 179.
50. For a review, see: Meijere, A.; Meyer, F. E. Angew Chem., Int. Ed. Engl. 1994, 33, 2379.
51. (a) Masters, J. J.; Jung, D. K.; Bornmann, W. G.; Danishefsky, S. J. Tetrahedron Lett. 1993, 34, 7253.
52. (b) Young, W. B.; Masters, J. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5228.
53. Masters, J. J. Unpublished results.
54. Young, W. B.; Link, J. T.; Masters, J. J., Snyder, L. B.; Danishefsky, S. J. Tetrahedron Lett. 1995, 36, 4963.
55. 4-Bn version of compound 100a formed through analogous chemistry via 91.
56. Nicolaou, K. C., Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409. Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1994, 295.
57. Nicolaou, K. C., Renaud, J.; Nantermet, P. G.; Couladouros, E. A.; Guy, R. K.; Wrasidlo, W. J. Am. Chem. Soc. 1995, 117, 2409. Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K. J. Chem. Soc., Chem. Commun. 1994, 295.
58. For a review on the uses of samarium diiodide, see: Molander, G. A. Chem. Rev. 1992, 92, 29.
59. Queneau, Y.; Krol, W. J.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1992, 57, 4043.
60. Cf: Ojima, I.; Sun, C. M.; Zucco, M ; Park, Y. H.; Duclos, O.; Kuduk, S. Tetrahedron Lett. 1993, 34, 4149. Ojima, I.; Habus, I ; Zucco, M.; Park, Y. M.; Sun, C. M.; Brigaud, T. Tetrahedron 1992, 48, 6985.
61. Cf: Ojima, I.; Sun, C. M.; Zucco, M ; Park, Y. H.; Duclos, O.; Kuduk, S. Tetrahedron Lett. 1993, 34, 4149. Ojima, I.; Habus, I ; Zucco, M.; Park, Y. M.; Sun, C. M.; Brigaud, T. Tetrahedron 1992, 48, 6985.
62. Enantiomerically pure 10 was generated via the same procedures as described for racemic 10: see ref 17.
63. Formation of side product 17 has been described previously: see ref 17.
64. Formation of side product 23 has been described previously; see ref 17.
65. Compound reported by Nicolaou; see: Nicolaou, K. C.; et al. J. Am. Chem. Soc. 1995, 117, 653-659.