A 2-pyridone photo-[4 + 4] approach to the taxanes

Journal of the American Chemical Society

Volumn 118, Issue 44, 1996, Pages 10803-10810

  Sieburth, Scott McN ^a   Chen, Jianhao ^a   Ravindran, Krishnamoorthy ^a   Chen, Jian Long ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0000382422     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962207r     Document Type: Article

References (70)

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38. The degree of difficulty for forming three or more tetrasubstituted carbons during a cycloaddition reaction can be calibrated by consulting some of the comprehensive cycloaddition reviews. A review of intramolecular Diels-Alder reactions (Ciganek, E. Org. React. (N. Y.) 1984, 32, 1-374) contains a single reference to a reaction forming four tetrasubstituted carbons: Paquette, L. A.; Wyvratt, M. J.; Berk, H. C.; Moerck, R. E. J. Am. Chem. Soc. 1978, 100, 5845-5855. Photo-[2 + 2] reactions are perhaps more generous, with a recent review (Crimmins, M. T.; Reinhold, T. L. Org. React. (N. Y.) 1993, 44, 297-588) including three systems that produce four tetrasubstituted carbons: Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543-4559. Reid, S. T.; De Silva, D. Tetrahedron Lett. 1983, 24, 1949-1950. De Keukeleire, D.; Van Audenhove, M.; Van Hijfte, L.; Audenaert, F.; Vandewalle, M. J. Photochem. 1985, 28, 165-174. Outstanding exceptions, of course, are the thermal [2 + 2] cycloaddition reactions of strained and polyfluorinated alkenes: Dolbier, W. R., Jr.; Lomas, D.; Garza, T.; Harmon, C.; Tarrant, P. Tetrahedron 1972, 28, 3185-3189. Huisgen, R.; Grashey, R.; Sauer, J. In The Chemistry of Alkenes; Patai, S., Ed.; Interscience: New York, 1964; pp 739-953. Roberts, J. D.; Sharts, C. M. Org. React. (N. Y.) 1962, 12, 1-56.
39. The degree of difficulty for forming three or more tetrasubstituted carbons during a cycloaddition reaction can be calibrated by consulting some of the comprehensive cycloaddition reviews. A review of intramolecular Diels-Alder reactions (Ciganek, E. Org. React. (N. Y.) 1984, 32, 1-374) contains a single reference to a reaction forming four tetrasubstituted carbons: Paquette, L. A.; Wyvratt, M. J.; Berk, H. C.; Moerck, R. E. J. Am. Chem. Soc. 1978, 100, 5845-5855. Photo-[2 + 2] reactions are perhaps more generous, with a recent review (Crimmins, M. T.; Reinhold, T. L. Org. React. (N. Y.) 1993, 44, 297-588) including three systems that produce four tetrasubstituted carbons: Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543-4559. Reid, S. T.; De Silva, D. Tetrahedron Lett. 1983, 24, 1949-1950. De Keukeleire, D.; Van Audenhove, M.; Van Hijfte, L.; Audenaert, F.; Vandewalle, M. J. Photochem. 1985, 28, 165-174. Outstanding exceptions, of course, are the thermal [2 + 2] cycloaddition reactions of strained and polyfluorinated alkenes: Dolbier, W. R., Jr.; Lomas, D.; Garza, T.; Harmon, C.; Tarrant, P. Tetrahedron 1972, 28, 3185-3189. Huisgen, R.; Grashey, R.; Sauer, J. In The Chemistry of Alkenes; Patai, S., Ed.; Interscience: New York, 1964; pp 739-953. Roberts, J. D.; Sharts, C. M. Org. React. (N. Y.) 1962, 12, 1-56.
40. The degree of difficulty for forming three or more tetrasubstituted carbons during a cycloaddition reaction can be calibrated by consulting some of the comprehensive cycloaddition reviews. A review of intramolecular Diels-Alder reactions (Ciganek, E. Org. React. (N. Y.) 1984, 32, 1-374) contains a single reference to a reaction forming four tetrasubstituted carbons: Paquette, L. A.; Wyvratt, M. J.; Berk, H. C.; Moerck, R. E. J. Am. Chem. Soc. 1978, 100, 5845-5855. Photo-[2 + 2] reactions are perhaps more generous, with a recent review (Crimmins, M. T.; Reinhold, T. L. Org. React. (N. Y.) 1993, 44, 297-588) including three systems that produce four tetrasubstituted carbons: Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543-4559. Reid, S. T.; De Silva, D. Tetrahedron Lett. 1983, 24, 1949-1950. De Keukeleire, D.; Van Audenhove, M.; Van Hijfte, L.; Audenaert, F.; Vandewalle, M. J. Photochem. 1985, 28, 165-174. Outstanding exceptions, of course, are the thermal [2 + 2] cycloaddition reactions of strained and polyfluorinated alkenes: Dolbier, W. R., Jr.; Lomas, D.; Garza, T.; Harmon, C.; Tarrant, P. Tetrahedron 1972, 28, 3185-3189. Huisgen, R.; Grashey, R.; Sauer, J. In The Chemistry of Alkenes; Patai, S., Ed.; Interscience: New York, 1964; pp 739-953. Roberts, J. D.; Sharts, C. M. Org. React. (N. Y.) 1962, 12, 1-56.
41. The degree of difficulty for forming three or more tetrasubstituted carbons during a cycloaddition reaction can be calibrated by consulting some of the comprehensive cycloaddition reviews. A review of intramolecular Diels-Alder reactions (Ciganek, E. Org. React. (N. Y.) 1984, 32, 1-374) contains a single reference to a reaction forming four tetrasubstituted carbons: Paquette, L. A.; Wyvratt, M. J.; Berk, H. C.; Moerck, R. E. J. Am. Chem. Soc. 1978, 100, 5845-5855. Photo-[2 + 2] reactions are perhaps more generous, with a recent review (Crimmins, M. T.; Reinhold, T. L. Org. React. (N. Y.) 1993, 44, 297-588) including three systems that produce four tetrasubstituted carbons: Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543-4559. Reid, S. T.; De Silva, D. Tetrahedron Lett. 1983, 24, 1949-1950. De Keukeleire, D.; Van Audenhove, M.; Van Hijfte, L.; Audenaert, F.; Vandewalle, M. J. Photochem. 1985, 28, 165-174. Outstanding exceptions, of course, are the thermal [2 + 2] cycloaddition reactions of strained and polyfluorinated alkenes: Dolbier, W. R., Jr.; Lomas, D.; Garza, T.; Harmon, C.; Tarrant, P. Tetrahedron 1972, 28, 3185-3189. Huisgen, R.; Grashey, R.; Sauer, J. In The Chemistry of Alkenes; Patai, S., Ed.; Interscience: New York, 1964; pp 739-953. Roberts, J. D.; Sharts, C. M. Org. React. (N. Y.) 1962, 12, 1-56.
42. The degree of difficulty for forming three or more tetrasubstituted carbons during a cycloaddition reaction can be calibrated by consulting some of the comprehensive cycloaddition reviews. A review of intramolecular Diels-Alder reactions (Ciganek, E. Org. React. (N. Y.) 1984, 32, 1-374) contains a single reference to a reaction forming four tetrasubstituted carbons: Paquette, L. A.; Wyvratt, M. J.; Berk, H. C.; Moerck, R. E. J. Am. Chem. Soc. 1978, 100, 5845-5855. Photo-[2 + 2] reactions are perhaps more generous, with a recent review (Crimmins, M. T.; Reinhold, T. L. Org. React. (N. Y.) 1993, 44, 297-588) including three systems that produce four tetrasubstituted carbons: Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543-4559. Reid, S. T.; De Silva, D. Tetrahedron Lett. 1983, 24, 1949-1950. De Keukeleire, D.; Van Audenhove, M.; Van Hijfte, L.; Audenaert, F.; Vandewalle, M. J. Photochem. 1985, 28, 165-174. Outstanding exceptions, of course, are the thermal [2 + 2] cycloaddition reactions of strained and polyfluorinated alkenes: Dolbier, W. R., Jr.; Lomas, D.; Garza, T.; Harmon, C.; Tarrant, P. Tetrahedron 1972, 28, 3185-3189. Huisgen, R.; Grashey, R.; Sauer, J. In The Chemistry of Alkenes; Patai, S., Ed.; Interscience: New York, 1964; pp 739-953. Roberts, J. D.; Sharts, C. M. Org. React. (N. Y.) 1962, 12, 1-56.
43. The degree of difficulty for forming three or more tetrasubstituted carbons during a cycloaddition reaction can be calibrated by consulting some of the comprehensive cycloaddition reviews. A review of intramolecular Diels-Alder reactions (Ciganek, E. Org. React. (N. Y.) 1984, 32, 1-374) contains a single reference to a reaction forming four tetrasubstituted carbons: Paquette, L. A.; Wyvratt, M. J.; Berk, H. C.; Moerck, R. E. J. Am. Chem. Soc. 1978, 100, 5845-5855. Photo-[2 + 2] reactions are perhaps more generous, with a recent review (Crimmins, M. T.; Reinhold, T. L. Org. React. (N. Y.) 1993, 44, 297-588) including three systems that produce four tetrasubstituted carbons: Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543-4559. Reid, S. T.; De Silva, D. Tetrahedron Lett. 1983, 24, 1949-1950. De Keukeleire, D.; Van Audenhove, M.; Van Hijfte, L.; Audenaert, F.; Vandewalle, M. J. Photochem. 1985, 28, 165-174. Outstanding exceptions, of course, are the thermal [2 + 2] cycloaddition reactions of strained and polyfluorinated alkenes: Dolbier, W. R., Jr.; Lomas, D.; Garza, T.; Harmon, C.; Tarrant, P. Tetrahedron 1972, 28, 3185-3189. Huisgen, R.; Grashey, R.; Sauer, J. In The Chemistry of Alkenes; Patai, S., Ed.; Interscience: New York, 1964; pp 739-953. Roberts, J. D.; Sharts, C. M. Org. React. (N. Y.) 1962, 12, 1-56.
44. The degree of difficulty for forming three or more tetrasubstituted carbons during a cycloaddition reaction can be calibrated by consulting some of the comprehensive cycloaddition reviews. A review of intramolecular Diels-Alder reactions (Ciganek, E. Org. React. (N. Y.) 1984, 32, 1-374) contains a single reference to a reaction forming four tetrasubstituted carbons: Paquette, L. A.; Wyvratt, M. J.; Berk, H. C.; Moerck, R. E. J. Am. Chem. Soc. 1978, 100, 5845-5855. Photo-[2 + 2] reactions are perhaps more generous, with a recent review (Crimmins, M. T.; Reinhold, T. L. Org. React. (N. Y.) 1993, 44, 297-588) including three systems that produce four tetrasubstituted carbons: Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543-4559. Reid, S. T.; De Silva, D. Tetrahedron Lett. 1983, 24, 1949-1950. De Keukeleire, D.; Van Audenhove, M.; Van Hijfte, L.; Audenaert, F.; Vandewalle, M. J. Photochem. 1985, 28, 165-174. Outstanding exceptions, of course, are the thermal [2 + 2] cycloaddition reactions of strained and polyfluorinated alkenes: Dolbier, W. R., Jr.; Lomas, D.; Garza, T.; Harmon, C.; Tarrant, P. Tetrahedron 1972, 28, 3185-3189. Huisgen, R.; Grashey, R.; Sauer, J. In The Chemistry of Alkenes; Patai, S., Ed.; Interscience: New York, 1964; pp 739-953. Roberts, J. D.; Sharts, C. M. Org. React. (N. Y.) 1962, 12, 1-56.
45. The degree of difficulty for forming three or more tetrasubstituted carbons during a cycloaddition reaction can be calibrated by consulting some of the comprehensive cycloaddition reviews. A review of intramolecular Diels-Alder reactions (Ciganek, E. Org. React. (N. Y.) 1984, 32, 1-374) contains a single reference to a reaction forming four tetrasubstituted carbons: Paquette, L. A.; Wyvratt, M. J.; Berk, H. C.; Moerck, R. E. J. Am. Chem. Soc. 1978, 100, 5845-5855. Photo-[2 + 2] reactions are perhaps more generous, with a recent review (Crimmins, M. T.; Reinhold, T. L. Org. React. (N. Y.) 1993, 44, 297-588) including three systems that produce four tetrasubstituted carbons: Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543-4559. Reid, S. T.; De Silva, D. Tetrahedron Lett. 1983, 24, 1949-1950. De Keukeleire, D.; Van Audenhove, M.; Van Hijfte, L.; Audenaert, F.; Vandewalle, M. J. Photochem. 1985, 28, 165-174. Outstanding exceptions, of course, are the thermal [2 + 2] cycloaddition reactions of strained and polyfluorinated alkenes: Dolbier, W. R., Jr.; Lomas, D.; Garza, T.; Harmon, C.; Tarrant, P. Tetrahedron 1972, 28, 3185-3189. Huisgen, R.; Grashey, R.; Sauer, J. In The Chemistry of Alkenes; Patai, S., Ed.; Interscience: New York, 1964; pp 739-953. Roberts, J. D.; Sharts, C. M. Org. React. (N. Y.) 1962, 12, 1-56.
46. The degree of difficulty for forming three or more tetrasubstituted carbons during a cycloaddition reaction can be calibrated by consulting some of the comprehensive cycloaddition reviews. A review of intramolecular Diels-Alder reactions (Ciganek, E. Org. React. (N. Y.) 1984, 32, 1-374) contains a single reference to a reaction forming four tetrasubstituted carbons: Paquette, L. A.; Wyvratt, M. J.; Berk, H. C.; Moerck, R. E. J. Am. Chem. Soc. 1978, 100, 5845-5855. Photo-[2 + 2] reactions are perhaps more generous, with a recent review (Crimmins, M. T.; Reinhold, T. L. Org. React. (N. Y.) 1993, 44, 297-588) including three systems that produce four tetrasubstituted carbons: Mehta, G.; Srikrishna, A.; Reddy, A. V.; Nair, M. S. Tetrahedron 1981, 37, 4543-4559. Reid, S. T.; De Silva, D. Tetrahedron Lett. 1983, 24, 1949-1950. De Keukeleire, D.; Van Audenhove, M.; Van Hijfte, L.; Audenaert, F.; Vandewalle, M. J. Photochem. 1985, 28, 165-174. Outstanding exceptions, of course, are the thermal [2 + 2] cycloaddition reactions of strained and polyfluorinated alkenes: Dolbier, W. R., Jr.; Lomas, D.; Garza, T.; Harmon, C.; Tarrant, P. Tetrahedron 1972, 28, 3185-3189. Huisgen, R.; Grashey, R.; Sauer, J. In The Chemistry of Alkenes; Patai, S., Ed.; Interscience: New York, 1964; pp 739-953. Roberts, J. D.; Sharts, C. M. Org. React. (N. Y.) 1962, 12, 1-56.
47. 7 conformations). Conformations in which the bonding carbons were more than 5 Å apart were rejected (> 99.98%), and for each saved conformation, the steric energy was calculated. Only those conformations within 10 kcal/mol of the lowest energy conformation were kept, giving 8594 conformations.
48. An identical conformational search with two methyl groups at the external (cross) positions of 11 clearly showed this steric interaction, with low-energy conformations highly distorted from that shown for 11 in Figure 1.
49. (a) Fujii, H.; Shiba, K.; Kaneko, C. J. Chem. Soc., Chem. Commun. 1980, 537-538.
50. (b) Kaneko, C.; Shiba, K.; Fujii, H.; Momose, Y. J. Chem. Soc., Chem. Commun. 1980, 1177-1178.
51. 11
52. A study of this intermolecular reaction has been reported, see: Sieburth, S. McN.; Lin, C.-H. Tetrahedron Lett. 1996, 37, 1141-1144.
53. Huckin, S. N.; Weiler, L. Can. J. Chem. 1974, 52, 1343-1351.
54. The low chemical shift for this methyl group appears to be associated with flanking oxygen and perhaps nitrogen substitution but not carbon or chlorine as can be seen in the chemical shifts of the following *methyl groups (chemical shift, Sadtler spectra reference number): 1,3-diamino-2-*methylbenzene (10.0 ppm, 6007C); 1,3-dihydroxy-2-*methylbenzene (8.5 ppm, 8762C); 1,3-dimethoxy-2-*methylbenzene (8.2 ppm, 4278C); *2,3-dimethyl-1-methoxybenzene (11.5 ppm, 9064C); 1,*2.3-trimethylbenzene (15.1 ppm, 3521C); 1,3-dichloro-2-*methylbenzene (17.2 ppm, 6281C).
55. Stork, G.; Maldonado, L. J. Am. Chem. Soc. 1971, 93, 5286-5287.
56. Tieckelmann, H. In Heterocyclic Compounds; Abramovitch, R. A., Ed.; John Wiley & Sons: New York, 1974; Vol. 14, Part 3, pp 683-694.
57. Standard hydrolytic procedures involving acidic or basic hydrolysis (see: Wibaut, J. P.; Haayman, P. W.; van Dijk, J. Recl. Trav. Chim. Pays-Bas 1940, 59, 202-206) did not lead to useful yields of the desired product.
58. Mukaiyama, T.; Usui, M.; Shimada, E.; Saigo, K. Chem. Lett. 1975, 1045-1048.
59. Isoxazolo[5,4-b]pyridines have most frequently been prepared by annulation of the pyridine onto a preformed isoxazole; see: Juric, P.; Kocevar, M.; Stanovnik, B.; Tisler, M.; Vercek, B. Chem. Scripta 1984, 23, 209-211 and references therein.
60. Oximes and oxime ethers generally have high barriers to E/Z isomerization. For discussion and lead references, see: Glaser, R.; Streitwieser, A. J. Org. Chem. 1989, 54, 5491-5502. Glaser, R.; Streitwieser, A. J. Am. Chem. Soc. 1989, 111, 7340-7348.
61. Oximes and oxime ethers generally have high barriers to E/Z isomerization. For discussion and lead references, see: Glaser, R.; Streitwieser, A. J. Org. Chem. 1989, 54, 5491-5502. Glaser, R.; Streitwieser, A. J. Am. Chem. Soc. 1989, 111, 7340-7348.
62. Curran, D. P. J. Am. Chem. Soc. 1983, 105, 5826-5833.
63. Previous hydrogenations of the isoxazolo[5,4-b]pyridine ring system have been reported to reduce both the N-O bond and the resulting pyridone ring; see: Skötsch, C.; Kohlmeyer, I.; Breitmaier, E. Synthesis 1979, 449-452; U.K. Patent GB 2, 117, 765, 1983; Chem. Abstr. 100:120892x.
64. Previous hydrogenations of the isoxazolo[5,4-b]pyridine ring system have been reported to reduce both the N-O bond and the resulting pyridone ring; see: Skötsch, C.; Kohlmeyer, I.; Breitmaier, E. Synthesis 1979, 449-452; U.K. Patent GB 2, 117, 765, 1983; Chem. Abstr. 100:120892x.
65. Photodimers of 2-pyridones have been reported to revert to the original 2-pyridones thermally (Meyers, A. I.; Singh, P. J. Org. Chem. 1970, 35, 3022-3030). A pathway for this decomposition could involve retroaldol of the β-amino carbonyls. Inspection of models suggests that the orbital alignment for this process would be good.
66. Sieburth, S. McN. J. Chem. Soc., Chem. Commun. 1994, 1663-1664.
67. Frimer, A. A. Synthesis 1977, 578-579.
68. For general experimental procedures, see ref 17.
69. Brewster, K.; Harrison, J. M.; Inch, T. D. J. Heterocycl. Chem. 1978, 15, 1497-1499.
70. Clark, M.; Cramer, R. D., III; Van Opdenbosch, N. J. Comput. Chem. 1989, 10, 982-1012.