Taxane diterpenes 2: Synthesis of the 7-deoxy ABC taxane skeleton, and reactions of the A-ring

Tetrahedron

Volumn 52, Issue 45, 1996, Pages 14103-14146

  Magnus, Philip ^a   Booth, John ^a   Diorazio, Louis ^a   Donohoe, Timothy ^a   Lynch, Vince ^a   Magnus, Nicholas ^a   Mendoza, José ^a   Pye, Philip ^a   Tarrant, James ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030569322     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00866-6     Document Type: Article

References (68)

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2. 1. Bauta, W. E.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T. J.; Frost, C.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J. G.; Thom. S.; Ujjainwalla, F. Tetrahedron, 1996, 52, 14081. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
3. 1. Bauta, W. E.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T. J.; Frost, C.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J. G.; Thom. S.; Ujjainwalla, F. Tetrahedron, 1996, 52, 14081. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
4. 1. Bauta, W. E.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T. J.; Frost, C.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J. G.; Thom. S.; Ujjainwalla, F. Tetrahedron, 1996, 52, 14081. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
5. 1. Bauta, W. E.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T. J.; Frost, C.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J. G.; Thom. S.; Ujjainwalla, F. Tetrahedron, 1996, 52, 14081. For preliminary communications of part of this work see:-Bauta, W.; Booth, J.; Bos, M. E.; DeLuca, M.; Diorazio, L.; Donohoe, T.; Magnus, N.; Magnus, P.; Mendoza, J.; Pye, P.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5327. Magnus, P.; Booth, J.; Magnus, N.; Tarrant, J.; Thom, S.; Ujjainwalla, F. Tetrahedron Lett. 1995, 36, 5331. Magnus, P.; Pye, P. J. C. S. Chem. Comm. 1995, 1933. Magnus, P.; Diorazio, L.; Donohoe, T.; Giles, M.; Pye, P.; J. Tarrant, J.; Thom, S. J. C. S. Chem. Comm. 1995, 1935.
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7. 2. Dauben, W. G.; Deviny, E. J. J. Org. Chem. 1966, 31, 3794. Zimmerman, H. E.; Hancock, K. G.; Licke, G. C. J. Am. Chem. Soc. 1968, 90, 4892. Stork, G.; Uyeo, S.; Wakamatsu, T.; Grieco, P. A.; Labovitz, J. J. Am. Chem. Soc. 1971, 93, 4945. In earlier studies it was found that treatment of the enone 6 with isopropylidenetriphenylphosphorane gave 6a, and exposure of 6a to the usual reductive cleavage conditions resulted in a mixture of 6b and 6c. It was concluded that an anion or radical stabilizing group at C-11 would change the course of the reductive cleavage and result in rupture of the internal cyclopropane bond. (equation presented)
8. 2. Dauben, W. G.; Deviny, E. J. J. Org. Chem. 1966, 31, 3794. Zimmerman, H. E.; Hancock, K. G.; Licke, G. C. J. Am. Chem. Soc. 1968, 90, 4892. Stork, G.; Uyeo, S.; Wakamatsu, T.; Grieco, P. A.; Labovitz, J. J. Am. Chem. Soc. 1971, 93, 4945. In earlier studies it was found that treatment of the enone 6 with isopropylidenetriphenylphosphorane gave 6a, and exposure of 6a to the usual reductive cleavage conditions resulted in a mixture of 6b and 6c. It was concluded that an anion or radical stabilizing group at C-11 would change the course of the reductive cleavage and result in rupture of the internal cyclopropane bond. (equation presented)
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12. 4. Through the processes of β,γ-Isomerization, autoxidation and C-3 epimerization we have introduced the C-1 to C-5 functionality in the 7-oxy series. Magnus, P.; Ujjainwalla, F.; Westwood, N.; Lynch, V. Tetrahedron Lett. 1996, submitted.
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14. 5. For the introduction of the 1β-hydroxyl group by oxidation of a C-1 enolate with a γ-lactone C-ring see:-Holton, R. A.; Somoza, C.; Kim, H.-B.; Liang, F.; Biediger, J.; Boatman, P. 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. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597. Shea, K. J.; Sakata, S. T. Tetrahedron Lett. 1992, 33, 4261. Autoxidation with a benzenoid C-ring, see:-Wender, P. A.; Mucciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878. Failure of autoxidation at C-1 with a 10β-OBn substituent, see:-Park, T. K.; Kim, I. J.; Danishefsky, S. J.; de Gala, S. Tetrahedron Lett. 1995, 36, 1019.
15. 5. For the introduction of the 1β-hydroxyl group by oxidation of a C-1 enolate with a γ-lactone C-ring see:-Holton, R. A.; Somoza, C.; Kim, H.-B.; Liang, F.; Biediger, J.; Boatman, P. 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. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597. Shea, K. J.; Sakata, S. T. Tetrahedron Lett. 1992, 33, 4261. Autoxidation with a benzenoid C-ring, see:-Wender, P. A.; Mucciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878. Failure of autoxidation at C-1 with a 10β-OBn substituent, see:-Park, T. K.; Kim, I. J.; Danishefsky, S. J.; de Gala, S. Tetrahedron Lett. 1995, 36, 1019.
16. 5. For the introduction of the 1β-hydroxyl group by oxidation of a C-1 enolate with a γ-lactone C-ring see:-Holton, R. A.; Somoza, C.; Kim, H.-B.; Liang, F.; Biediger, J.; Boatman, P. 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. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1597. Shea, K. J.; Sakata, S. T. Tetrahedron Lett. 1992, 33, 4261. Autoxidation with a benzenoid C-ring, see:-Wender, P. A.; Mucciaro, T. P. J. Am. Chem. Soc. 1992, 114, 5878. Failure of autoxidation at C-1 with a 10β-OBn substituent, see:-Park, T. K.; Kim, I. J.; Danishefsky, S. J.; de Gala, S. Tetrahedron Lett. 1995, 36, 1019.
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49. 20. Lombarde, L. Tetrahedron Lett. 1982, 23, 4293. Takai, K.; Motta, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1978, 19, 2417. Hibino, J.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5579. Tebbe, F.N.; Parshall, G.W.; Reddy, G.S. J. Am. Chem. Soc. 1978, 100, 3611. Schrock, R.R. J. Am. Chem. Soc. 1976, 98, 5399. Cannizzo, L.F.; Grubbs, R.H. J. Org. Chem. 1985, 50, 2386.
50. 21. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313.
51. 21. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1980, 21, 4313.
52. 22. Rawal, V. H.; Dufour, C.; Eschbach, A. J. Chem. Soc., Chem. Comm. 1994, 1797. Professor Rawal is thanked for advice concerning this procedure.
53. 23. Datta, A.; Jayasinghe, L. R.; Georg, G. I. J. Org. Chem. 1994, 59, 4689. Georg, G. I.; Ali, S. M.; Boge, T. C.; Datta, A.; Falborg, L. Tetrahedron Lett. 1994, 35, 8931.
54. 23. Datta, A.; Jayasinghe, L. R.; Georg, G. I. J. Org. Chem. 1994, 59, 4689. Georg, G. I.; Ali, S. M.; Boge, T. C.; Datta, A.; Falborg, L. Tetrahedron Lett. 1994, 35, 8931.
55. 24. Paquette has reported the conversion of a 14-ketotaxane into the corresponding 13,14-dione using oxaziridine methodology. Elmore, S. W.; Paquette, L. A. J. Org. Chem. 1993, 58, 4963.
56. 25. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 44. Rosini, G.; Ballini, R., Synthesis 1988, 833. Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294.
57. 25. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 44. Rosini, G.; Ballini, R., Synthesis 1988, 833. Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294.
58. 25. Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 44. Rosini, G.; Ballini, R., Synthesis 1988, 833. Corey, E. J.; Estreicher, H. J. Am. Chem. Soc. 1978, 100, 6294.
59. 26. Cope, A. C.; Martin, M. M.; McKervey, M. A. Quarterly Reviews Chem. Soc. 1966, Vol XX, 119. Essig, M. G.; Stevenson, T. T.; Shafizadeh, F.; Stenkamp, R. E.; Jenson, L. H. J. Org. Chem. 1984, 49, 3652. Calvert, B. J.; Hobson, J. D. J. Chem. Soc. 1965, 2723. Warnhoff, E. W.; Reynolds-Warnhoff, P.; Wong, M. Y. H. J. Amer. Chem. Soc. 1980, 102, 5956. Watt, I.; Whittleton, S. N.; Whitworth, S. M. Tetrahedron 1986, 42, 1047.
60. 26. Cope, A. C.; Martin, M. M.; McKervey, M. A. Quarterly Reviews Chem. Soc. 1966, Vol XX, 119. Essig, M. G.; Stevenson, T. T.; Shafizadeh, F.; Stenkamp, R. E.; Jenson, L. H. J. Org. Chem. 1984, 49, 3652. Calvert, B. J.; Hobson, J. D. J. Chem. Soc. 1965, 2723. Warnhoff, E. W.; Reynolds-Warnhoff, P.; Wong, M. Y. H. J. Amer. Chem. Soc. 1980, 102, 5956. Watt, I.; Whittleton, S. N.; Whitworth, S. M. Tetrahedron 1986, 42, 1047.
61. 26. Cope, A. C.; Martin, M. M.; McKervey, M. A. Quarterly Reviews Chem. Soc. 1966, Vol XX, 119. Essig, M. G.; Stevenson, T. T.; Shafizadeh, F.; Stenkamp, R. E.; Jenson, L. H. J. Org. Chem. 1984, 49, 3652. Calvert, B. J.; Hobson, J. D. J. Chem. Soc. 1965, 2723. Warnhoff, E. W.; Reynolds-Warnhoff, P.; Wong, M. Y. H. J. Amer. Chem. Soc. 1980, 102, 5956. Watt, I.; Whittleton, S. N.; Whitworth, S. M. Tetrahedron 1986, 42, 1047.
62. 26. Cope, A. C.; Martin, M. M.; McKervey, M. A. Quarterly Reviews Chem. Soc. 1966, Vol XX, 119. Essig, M. G.; Stevenson, T. T.; Shafizadeh, F.; Stenkamp, R. E.; Jenson, L. H. J. Org. Chem. 1984, 49, 3652. Calvert, B. J.; Hobson, J. D. J. Chem. Soc. 1965, 2723. Warnhoff, E. W.; Reynolds-Warnhoff, P.; Wong, M. Y. H. J. Amer. Chem. Soc. 1980, 102, 5956. Watt, I.; Whittleton, S. N.; Whitworth, S. M. Tetrahedron 1986, 42, 1047.
63. 26. Cope, A. C.; Martin, M. M.; McKervey, M. A. Quarterly Reviews Chem. Soc. 1966, Vol XX, 119. Essig, M. G.; Stevenson, T. T.; Shafizadeh, F.; Stenkamp, R. E.; Jenson, L. H. J. Org. Chem. 1984, 49, 3652. Calvert, B. J.; Hobson, J. D. J. Chem. Soc. 1965, 2723. Warnhoff, E. W.; Reynolds-Warnhoff, P.; Wong, M. Y. H. J. Amer. Chem. Soc. 1980, 102, 5956. Watt, I.; Whittleton, S. N.; Whitworth, S. M. Tetrahedron 1986, 42, 1047.
64. 27. We have shown (7-oxy series) that the hydride migration is reversible (see reference 4).
65. 28. Treatment of 82 with LDA/THF/60°C results in conversion to a mixture that does not contain 83, but we were unable separate the compounds and it was not pursued further.
66. 29. For reviews that outline the main strategies that have been used see:-Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem. Int. Ed. Engl. 1994, 33, 15. Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. "Recent Progress in the Synthesis of Taxanes", Contemporary Organic Synthesis, 1994, 1, 47. Paquette, L. A. "Studies Directed towards the Total Synthesis of Taxanes". Studies in Natural Product Chemistry, Ed. Rahman, A-ur. 1992, Vol 11, p. 3. Elsevier Science Publ. See also reference 11.
67. 29. For reviews that outline the main strategies that have been used see:-Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem. Int. Ed. Engl. 1994, 33, 15. Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. "Recent Progress in the Synthesis of Taxanes", Contemporary Organic Synthesis, 1994, 1, 47. Paquette, L. A. "Studies Directed towards the Total Synthesis of Taxanes". Studies in Natural Product Chemistry, Ed. Rahman, A-ur. 1992, Vol 11, p. 3. Elsevier Science Publ. See also reference 11.
68. 29. For reviews that outline the main strategies that have been used see:-Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem. Int. Ed. Engl. 1994, 33, 15. Boa, A. N.; Jenkins, P. R.; Lawrence, N. J. "Recent Progress in the Synthesis of Taxanes", Contemporary Organic Synthesis, 1994, 1, 47. Paquette, L. A. "Studies Directed towards the Total Synthesis of Taxanes". Studies in Natural Product Chemistry, Ed. Rahman, A-ur. 1992, Vol 11, p. 3. Elsevier Science Publ. See also reference 11.