Asymmetric Nitroaldol Reaction. Synthesis of Taxotere Side Chain and (-)-Bestatin Using (1R)-8-Phenylmenthyl Glyoxylate

Journal of Organic Chemistry

Volumn 69, Issue 8, 2004, Pages 2844-2850

  Kudyba, Iwona ^a   Raczko, Jerzy ^a   Jurczak, Janusz ^a,b  

^a POLISH ACADEMY OF SCIENCES   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ETHANE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ADDUCTS; STEREOSELECTIVITY;

METHANE;

1 NITRO 1 PHENYLMETHANE; 1 NITRO 2 PHENYLETHANE; 8 PHENYLMENTHYL GLYOXYLATE; BENZENE DERIVATIVE; BESTATIN; DOCETAXEL; GLYOXYLIC ACID DERIVATIVE; METHANE; PACLITAXEL; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 1842789682     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0358269     Document Type: Article

References (91)

1. (a) Jauristi, E.; Quintana, D.; Escalante, J. Aldrichchim. Acta 1994, 27, 3.
2. (b) Cole, D. C. Tetrahedron 1994, 50, 9517.
3. (c) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 29, 117.
4. (d) Andruszkiewicz, R. Pol. J. Chem. 1998, 72, 1 and references therein.
5. (a) Babine, R. L.; Bender, S. E. Chem. Rev. 1997, 97, 1359.
6. (b) Umezawa, H.; Aoyagi, T.; Suda, H.; Hamada, M.; Takieuchi, T. J. Antibiot. 1976, 29, 97.
7. (c) Nakamura, H.; Suda, H.; Takita, T.; Aoyagi, T.; Umezawa, H.; Iitaka, Y. J. Antibiot. 1976, 29, 102.
8. (d) Umezawa, K.; Ikeda, Y.; Uchihata, Y.; Naganawa, H.; Kondo, S. J. Org. Chem. 2000, 65, 459.
9. Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
10. (a) Rubin, A. E.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2637.
11. (b) Keding, S. J.; Dales; N. A.; Lim, S.; Beaulieu, D.; Rich, D. H. Synth. Commun. 1998, 28, 4463.
12. (c) Upadhya, T. T.; Sudalai, A. Tetrahedron: Asymmetry 1997, 8, 3685.
13. (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1993, 1375.
14. (e) Kato, K.; Saino, T.; Nishizawa, R.; Takita, T.; Umezawa, H. J. Chem. Soc., Perkin Trans. 1 1980, 1618.
15. (a) Nozaki, K.; Sato, N.; Takaya, H. Tetrahedron: Asymmetry 1993, 4, 2179.
16. (b) Patel, R. N.; Banerjee, A.; Howell, J. M.; McNamee, C. G.; Brzozowski, D.; Mirfakhrae, D.; Nanduri, V.; Thottathil, J. K.; Szarka, L. J. Tetrahedron: Asymmetry 1993, 4, 2069.
17. (c) Kearns, J.; Kayser, M. M. Tetrahedron Lett. 1994, 35, 2845.
18. (d) Wasserman, H. H.; Xia, M.; Petersen, A. K.; Jorgensen, M. R.; Curtis, E. A. Tetrahedron Lett. 1999, 40, 6163.
19. (e) Wasserman, H. H.; Xia, M.; Petersen, A. K. Tetrahedron 2003, 59, 6771.
20. (a) Herranz, R.; Castro-Pichel, J.; Vinnesa, S.; Garcia Lopez, M. T. J. Org. Chem. 1990, 55, 2232.
21. (b) Matsuda, F.; Matsumoto, T.; Ohsaki, M.; Ito, Y.; Terashima, S. Chem. Lett. 1990, 723.
22. (c) Denis, J.-N.; Correa, A.; Greene, A. E. J. Org. Chem. 1991, 56, 6939.
23. (d) Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181.
24. (e) Rich, D. H.; Moon, B. J.; Boparai, A. S. J. Org. Chem. 1980, 45, 2288.
25. (f) Takemoto, Y.; Matsumoto, T.; Ito, Y.; Terashima, S. Tetrahedron Lett. 1990, 31, 217.
26. (g) Manickam, G.; Nogami, H.; Kanai, M.; Gröger, H.; Shibasaki, M. Synlett 2001, 617.
27. Lee, H. J.; Lee, B. W.; Jang, K. C.; Kang, J. E.; Kim, J. H.; Park, K.-M.; Park, K. H. Tetrahedron Lett. 2003, 44, 5905.
28. Raghavan, S.; Rasheed, M. A. Tetrahedron: Asymmetry 2003, 14, 1371.
29. (a) Hagihara, M.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6570.
30. (b) Iwanowicz, E. J.; Lin, J.; Roberts, D. G. M.; Michael, I. M.; Seiler, S. M. Bioorg. Med. Chem. Lett. 1992, 2, 1607.
31. (a) Matsumoto, T.; Kobayashi, Y.; Takemoto, Y.; Ito, Y.; Kamijo, T.; Harada, H.; Terashima, S. Tetrahedron Lett. 1990, 31, 4175.
32. (b) Cativiela, C.; Diaz-de-Villegas, M. D.; Gálvez, J. A. Tetrahedron: Asymm. 1996, 7, 529.
33. (c) Ha, H.-J.; Ahn, Y.-G.; Woo, J.-S., Lee, G. S.; Lee, W. K. Bull. Chem. Soc. Jpn. 2001, 74, 1667.
34. (a) Swindell, C. S.; Tao, M. J. J. Org. Chem. 1993, 58, 5889.
35. (b) Kobayashi, Y.; Takemoto, Y.; Ito, S. Tetrahedron Lett. 1990, 31, 3031.
36. (c) Palomo, C.; Arrieta, A.; Cossio, F. P.; Aizpurua, J. M.; Mielgo, A.; Aurrekoetxea, N. Tetrahedron Lett. 1990, 31, 6429.
37. (d) Ito, Y.; Kamijo, T.; Harada, H.; Terashima, S. Heterocycles 1990, 30, 299.
38. (a) Denis, J.-N.; Greene, A. E.; Serra, A. A.; Luche, M.-J. J. Org. Chem. 1986 51, 46.
39. (b) Deng, L.; Jacobsen E. N. J. Org. Chem. 1992, 57, 4320.
40. (c) Commerçon, A.; Bézard, D.; Bernard, F.; Bourzat, J. D. Tetrahedron Lett. 1992, 33, 5185.
41. (d) Gou, D.-M.; Liu, Y.-C.; Chen, C.-S. J. Org. Chem. 1993, 58, 1287.
42. (e) Righi, G.; Chionne, A.; D'Achille, R.; Bonini, C. J. Tetrahedron: Asymmetry 1997, 8, 903.
43. (f) Grosjean, F.; Huehé, M.; Larehevêque, M.; Legendre, J. J.; Petit, Y. Tetrahedron 1994, 50, 9325.
44. (g) Pastó, M.; Castejón, P.; Moyano, A.; Pericas, M. A.; Riera, A. J. J. Org. Chem. 1996, 61, 6033.
45. (h) Legters, J.; Van Dienst, E.; Lambertus, T.; Zwanenburg, B. Rec. Trav. Chim. Pays-Bas 1992, 111, 69.
46. (a) Bourzat, J. D.; Commerçon, A. Tetrahedron Lett. 1993, 34, 6049.
47. (b) Palomo, C.; Aizpurua, J. M.; Miranda, J. I.; Mielgo, A.; Odriozola, J. M. Tetrahedron Lett. 1993, 34, 6326.
48. (c) Georg, G. I.; Cheruvallath, Z. S.; Harriman, G. C. B.; Hepperle, M.; Park, H. Bioorg. Med. Chem. Lett. 1993, 3, 2467.
49. (d) Holton, R. A.; Lin, J. H. Bioorg. Med. Chem. Lett. 1993, 3, 2475.
50. (e) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377.
51. Kobayashi, S.; Osobe, T.; Ohno, M. Tetrahedron Lett. 1984, 25, 5079.
52. Lee, H. J.; Lee, B. W.; Jang, K. C.; Jeong, I. Y.; Yang, M. S.; Lee, S. G.; Park, K. H. Synthesis 2003, 829.
53. (a) Norman, B. H.; Morris, M. L. Tetrahedron Lett. 1992, 33, 6803.
54. (b) Jefford, C. W.; Wang, J. B.; Lu, Z.-H. Tetrahedron Lett. 1993, 34, 7557.
55. (c) Tsuda, M.; Muraoka, Y.; Takeuchi, T. J. Antibiot. 1996, 49, 1031.
56. (d) Caputo, R.; Cecere, G.; Guaragna, A.; Palumbo, G.; Pedatella, S. Eur. J. Org. Chem. 2002, 350.
57. (a) Kudyba, I.; Raczko, J.; Jurczak, J. Tetrahedron Lett. 2003, 44, 8681.
58. (b) Kudyba, I.; Raczko, J.; Jurczak, J. Tetrahedron Lett. 2003, 44, 8685.
59. (c) Kudyba, I. Ph.D. Dissertation, Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, 2002.
60. For the synthesis of Taxol or Taxotere side chain, see: (a) Denis, J.-N. ; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957.
61. (b) Mukai, C.; Kim, I. J.; Furu, E.; Hanaoka, M. Tetrahedron 1993, 49, 8323.
62. (c) Koskinen, A. M. P.; Karvinen, E. K.; Siirilä, J. P. J. Chem. Soc., Chem. Commun. 1994, 21.
63. (d) Bunnage, M. E.; Davies, S. G.; Goodwin, C. J. J. Chem. Soc., Perkin Trans. 1 1994, 2385.
64. (e) Cabon, O.; Buisson, D.; Larchevêque, M.; Azerad, R. Tetrahedron: Asymmetry 1995, 6, 2211.
65. (f) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331.
66. (g) Pastó, M.; Moyano, A.; Pericas, M. A.; Riera, A. J. Tetrahedron: Asymmetry 1996, 7, 243.
67. (h) Hanessian, S.; Sancéau, J.-Y. Can. J. Chem. 1996, 74, 621.
68. (i) Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483.
69. (j) Harada, N.; Hashiyama, T.; Ozaki, K.; Yamaguchi, T.; Ando, A.; Tsujihara, K. Heterocycles 1997, 44, 305.
70. (k) Gennari C.; Carcano, M.; Donghi, M.; Mongelli, N.; Vanotti, E.; Vulpetti, A. J. Org. Chem. 1997, 62, 4746.
71. (l) Merino, P.; Castillo, E.; Franco, S.; Merchán, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301.
72. (m) Ojima, I.; Wang, H.; Wang, T.; Ng, E. W. Tetrahedron Lett. 1998, 39, 923.
73. (n) Ha, H. J.; Park, G. S.; Ahn, Y.-G.; Lee, S. G.; Bioorg. Med. Chem. Lett. 1998, 1619.
74. (o) Lee, S.-H.; Yoon, J.; Chung, S.-H.; Lee, Y.-S. Tetrahedron 2001, 57, 2139.
75. (p) Hamamoto, H.; Mamedov, V. A.; Kitamoto, M.; Hayashi, N.; Tsuboi, S. Tetrahedron: Asymmetry. 2000, 11, 4485.
76. (r) Choudary, B. M.; Chowdari, N. S.; Madhi, S.; Kantam, M. L. J. Org. Chem. 2003, 68, 1736.
77. (s) Schade, W.; Reissig, H.-U. J. Prakt. Chem. 1999, 341, 685.
78. (a) Einsenhauer, E. A.; Vermorken, J. F. Durgs 1998, 55, 5.
79. (b) Ojima, I.; Lin, S. N.; Wang, T. Curr. Med. Chem. 1999, 6, 927.
80. (c) Gueritte, F. Curr. Pharma. Design 2001, 7, 1229.
81. Kudyba, I.; Raczko, J.; Jurczak, J. Manuscript in preparation.
82. Deng, J.; Hamada, Y.; Shioiri, T. Synthesis 1998, 633.
83. For the synthesis of (-)-bestatin, see: (a) Pearson, W. H.; Hines, J. H. J. Org. Chem. 1989, 54, 4235.
84. (b) Palomo, C.; Aizpurua, J. M.; Cuevas, C. J. Chem. Soc., Chem. Commun. 1994, 1957.
85. (c) Koseki, K.; Ebata, T.; Matsushita, H. Biosc. Biotechnol. Biochem. 1996, 60, 534.
86. (d) Seki, M.; Nakao, K. Biosc. Biotechnol. Biochem. 1999, 63, 1304.
87. (e) Bergmeier, S. C.; Stanchina, D. M. J. Org. Chem. 1999, 64, 4235.
88. (f) Semple, J. E.; Owens, T. D.; Nguen, K.; Levy, O. E. Org. Lett. 2000, 2, 2769.
89. (g) Nemato, H.; Ma, R.; Suzuki, I.; Shibuya, M. Org. Lett. 2000, 2, 4245.
90. (e) Righi, G.; D'Achille, D.; Pescatore, G.; Bonini, C. J. Tetrahedron Lett. 2003, 44, 6999.
91. Ino, K.; Goto, S.; Nomura, S.; Isobe, K.-I.; Nawa, A.; Okamoto, T.; Tomoda, Y. Anticancer Res. 1995, 15, 2081.