Regioselective synthesis of nitrones by decarboxylative oxidation of N- alkyl-α-amino acids and application to the synthesis of 1-azabicyclic alkaloids

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 12, 1999, Pages 2737-2754

  Ohtake, Hiroaki ^a   Imada, Yasushi ^b   Murahashi, Shun Ichi ^b  

^a ASTELLAS PHARMA INC   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; AMINO ACID DERIVATIVE; BICYCLO COMPOUND; NITRONE DERIVATIVE; PYRROLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DECARBOXYLATION; DIASTEREOISOMER; ENANTIOMER; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033435238     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.2737     Document Type: Article

References (120)

1. a) J. Hamer and A. Macaluso, Chem. Rev., 64, 473 (1964).
2. b) G. R. Delpierre and M. Lamchen, Quart. Rev., 19, 329 (1965).
3. c) G. Tennant, "Comprehensive Organic Chemistry," ed by D. H. R. Barton and W. D. Ollis, Pergamon Press, Oxford (1979), Vol. 2, pp. 500-510.
4. d) E. Breuer, "Nitrones, Nitronates and Nitroxides," ed by S. Patai and Z. Rappoport, Wiley, New York (1989), Chaps. 2 and 3, pp. 139-312.
5. a) E. G. Janzen and D. L. Haire, "Advances in Free Radical Chemistry," ed by D. D. Tanner, JAI Press, Greenwich (1990), pp. 253-295.
6. b) E. G. Janzen, Acc. Chem. Res., 4, 31 (1971).
7. a) J. J. Tufariello, "1, 3-Dipolar Cycloaddition Chemistry," ed by A. Padwa, Wiley, New York (1984), Vol. 9, pp. 83-168.
8. b) A. Padwa, "1, 3-Dipolar Cycloaddition Chemistry," ed by A. Padwa, Wiley, New York (1984), Vol. 12, pp. 277-406.
9. c) K. B. G. Torssell, "Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis," VCH Publishers, New York (1988), Chap. 5, pp. 129-270.
10. d) P. N. Confalone and E. M. Huie, "The [3+2] Nitrone-Olefin Cycloaddition Reaction," ed by A. S. Kende, Wiley, New York (1988), Vol. 36, pp. 1-173.
11. e) W. Carruthers, "Cycloaddition Reactions in Organic Synthesis," ed by J. E. Baldwin, Pergamon Press, Oxford (1990), pp. 298-331.
12. f) K. V. Gothelf and K. A. Jørgensen, Chem. Rev., 98, 863 (1998).
13. Enantioselective 1,3-dipolar cycloadditions: a) W. W. Ellis, A. Gavrilova, L. L. -Sands, A. L. Rheingold, and B. Bosnich, Organometallics, 18, 332 (1999).
14. b) H. C. Aspinall, N. Greeves, and P. M. Smith, Tetrahedron Lett., 40, 1763 (1999).
15. c) S. Kanemasa, Y. Oderaotoshi, J. Tanaka, and E. Wada, J. Am. Chem. Soc., 120, 12355 (1998).
16. d) K. B. Simonsen, P. Bayón, R. G. Hazell, K. V. Gothelf, and K. A. Jørgensen, J. Am. Chem. Soc., 121, 3845 (1999).
17. e) S. Kobayashi, R. Akiyama, M. Kawamura, and H. Ishitani, Chem. Lett., 1997, 1039.
18. f) K. Hori, J. Ito, T. Ohta, and I. Furukawa, Tetrahedron, 54, 12737 (1998).
19. g) J.-P. G. Seerden, M. M. M. Boeren, and H. W. Scheeren, Tetrahedron, 53, 11843 (1997).
20. N. Risch and M. Arend, "Stereoselective Synthesis," ed by G. Helmchen, R. W. Hoffmann, J. Mulzer, and E. Schaumann, Georg Thieme Verlag, New York (1996), E 21, Vol. 3, Chap. 1.4.1.7, pp. 1887-1893.
21. Grignard reagents: a) Z.-Y. Chang and R. M. Coates, J. Org. Chem., 55, 3464 (1990). Metalated thiazoles:
22. b) A. Dondoni, S. Franco, F. Junquera, F. L. Merchán, P. Merino, T. Tejero, and V. Bertolasi, Chem. Eur. J., 1, 505 (1995). Chiral sulfoxide anion:
23. c) S.-I. Murahashi, J. Sun, and T. Tsuda, Tetrahedron Lett., 34, 2645 (1993). Alkylzinc compounds:
24. d) Y. Ukaji, Y. Kenmoku, and K. Inomata, Tetrahedron: Asymmetry, 7, 53 (1996). Hydrosilane:
25. e) S.-I. Murahashi, S. Watanabe, and T. Shiota, J. Chem. Soc., Chem. Commun., 1994, 725.
26. Alkaloids: a) S.-I. Murahashi, Y. Imada, M. Kohno, and T. Kawakami, Synlett, 1993, 395.
27. b) C. Louis and C. Hootelé, Tetrahedron: Asymmetry, 8, 109 (1997).
28. c) S. Chackalamannil and Y. Wang, Tetrahedron, 53, 11203 (1997).
29. d) A. B. Holmes, A. B. Hughes, A. L. Smith, and S. F. Williams, J. Chem. Soc., Perkin Trans. 1, 1992, 1089.
30. e) J. J. Tufariello, Acc. Chem. Res., 12, 396 (1979). β-Lactams:
31. f) M. Ihara, M. Takahashi, K. Fukumoto, and T. Kametani, J. Chem. Soc., Perkin Trans. 1, 1989, 2215.
32. g) M. E. Jung and B. T. Vu, J. Org. Chem., 61, 4427 (1996). Antibiotics:
33. h) P. DeShong, W. Li, J. W. Kennington, Jr., H. L. Ammon, and J. M. Leginus, J. Org. Chem., 56, 1364 (1991).
34. S.-I. Murahashi, H. Mitsui, T. Watanabe, and S. Zenki, Tetrahedron Lett., 24, 1049 (1983).
35. H. Staudinger and K. Miescher, Helv. Chim. Acta, 2, 554 (1919).
36. 2:
37. 2:
38. c)S. Cicchi, F. Cardona, A. Brandi, M. Corsi, and A. Goti, Tetrahedron Lett., 40, 1989 (1999).
39. S. R. Sandler and W. Karo, "Organic Functional Group Preparations," ed by H. H. Wasserman, Academic Press, New York (1986), Vol. 3, pp. 351-376.
40. Michael addition of oximes to electron-deficient alkenes: a) P. Armstrong, R. Grigg, and W. J. Warnock, J. Chem. Soc., Chem. Commun., 1987, 1325.
41. b) P. Armstrong, R. Grigg, S. Surendrakumar, and W. J. Warnock, J. Chem. Soc., Chem. Commun., 1987, 1327. Alkylation of oximes:
42. c) P. A. S. Smith and J. E. Robertson, J. Am. Chem. Soc., 84, 1197 (1962).
43. d) E. Buehler, J. Org. Chem., 32, 261 (1967).
44. S. R. Sandler and W. Karo, "Organic Functional Group Preparations," ed by H. H. Wasserman, Academic Press, New York (1986), Vol. 3, pp. 378-430.
45. a) H. Mitsui, S. Zenki, T. Shiota, and S.-I. Murahashi, J. Chem. Soc., Chem. Commun., 1984, 874.
46. b) S.-I. Murahashi, H. Mitsui, T. Shiota, T. Tsuda, and S. Watanabe, J. Org. Chem., 55, 1736 (1990).
47. c) S.-I. Murahashi, T. Shiota, and Y. Imada, Org. Synth., 70, 265 (1992).
48. S.-I. Murahashi and T. Shiota, Tetrahedron Lett., 28, 2383 (1987).
49. 2: E. Marcantoni, M. Petrini, and O. Polimanti, Tetrahedron Lett., 36, 3561 (1995).
50. 2: a) S. Sakaue, Y. Sakata, Y. Nishiyama, and Y. Ishii, Chem. Lett., 1992, 289.
51. 2:
52. c) R. W. Murray, K. Iyanar, J. Chen, and J. T. Wearing, J. Org. Chem., 61, 8099 (1996).
53. d) A. Goti and L. Nannelli, Tetrahedron Lett., 37, 6025 (1996).
54. 2:
55. f) R. Joseph, A. Sudalai, and T. Ravindranathan, Synlett, 1995, 1177.
56. a) R. Ballini, E. Marcantoni, and M. Petrini, J. Org. Chem., 57, 1316 (1992).
57. b) A. E. McCaig and R. H. Wightman, Tetrahedron Lett., 34, 3939 (1993).
58. c) W. Oppolzer and E. Merifield, Helv. Chim. Acta, 76, 957 (1993).
59. d) S. Cicchi, I. Höld, and A. Brandi, J. Org. Chem., 58, 5274 (1993).
60. e) W. Oppolzer, C. G. Bochet, and E. Merifield, Tetrahedron Lett., 35, 7015 (1994).
61. f) W. Oppolzer, J. Deerberg, and O. Tamura, Helv. Chim. Acta, 77, 554 (1994).
62. g) R. Giovannini, E. Marcantoni, and M. Petrini, J. Org. Chem., 60, 5706 (1995).
63. h) W. Oppolzer and C. G. Bochet, Tetrahedron Lett., 36, 2959 (1995).
64. i) A. E. McCaig, K. P. Meldrum, and R. H. Wightman, Tetrahedron, 54, 9429 (1998).
65. j) F. Cardona, S. Valenza, S. Picasso, A. Goti, and A. Brandi, J. Org. Chem., 63, 7311 (1998).
66. k) A. Goti, M. Cacciarini, F. Cardona, and A. Brandi, Tetrahedron Lett., 40, 2853 (1999).
67. Synthesis of biologically active heterocycles by using chiral cyclic nitrones: a) A. Goti, F. Cardona, A. Brandi, S. Picasso, and P. Vogel, Tetrahedron: Asymmetry, 7, 1659 (1996).
68. b) A. Goti, F. Cardona, and A. Brandi, Synlett, 1996, 761.
69. c) S. Chackalamannil and Y. Wang, Tetrahedron, 53, 11203 (1997).
70. d) M. Closa and R. H. Wightman, Synth. Commun., 28, 3443 (1998).
71. The preliminary results: a) S.-I. Murahashi, Y. Imada, and H. Ohtake, J. Org. Chem., 59, 6170 (1994).
72. b) S.-I. Murahashi, H. Ohtake, and Y. Imada, Tetrahedron Lett., 39, 2765 (1998).
73. a) Y. Ohfune, N. Kurokawa, N. Higuchi, M. Saito, M. Hashimoto, and T. Tanaka, Chem. Lett., 1984, 441.
74. b) P. Quitt, J. Hellerbach, and K. Vogler, Helv. Chim. Acta. 46, 327 (1963).
75. a) K. Harada and T. Okawara, Bull. Chem. Soc. Jpn., 46, 191 (1973).
76. b) I. Ojima, S. Inaba, and K. Nakatsugawa, Chem. Lett., 1975, 331.
77. Pyrrolizidine alkaloids: a) Y. Nishimura, "Studies in Natural Products Chemistry," ed by A. Rahman, Elsevier, Amsterdam (1988), Vol. I, pp. 227-303.
78. b) D. J. Robins, Nat. Prod. Rep., 11, 613 (1994).
79. c) M. Ikeda, T. Sato, and H. Ishibashi, Heterocycles, 27, 1465 (1988).
80. d) W. Dai, Y. Nagao, and E. Fujita, Heterocycles, 30, 1231 (1990).
81. Indolizidine alkaloids: a) D. J. Robins, "Rodd's Chemistry of Carbon Compounds," ed by M. F. Ansell, Elsevier, Amsterdam (1985), Vol. IV, Chap. 8.
82. b) J. P. Michael, Nat. Prod. Rep., 11, 639 (1994).
83. c) H. Takahata and T. Momose, "The Alkaloids; Chemistry and Pharmacology," ed by G. A. Cordell, Academic Press, New York (1993), Vol. 44, Chap. 3.
84. d) Y. Nishimura, "Studies in Natural Products Chemistry," ed by A. Rahman, Elsevier, Amsterdam (1988), Vol. I, pp. 227-303.
85. A. G. M. Barrett and D. Pilipauskas, J. Org. Chem., 56, 2787 (1991).
86. M. M. Bowers-Nemia and M. M. Joullié, Heterocycles, 20, 817 (1983).
87. S. Mori, T. Ohno, H. Harada, T. Aoyama, and T. Shioiri, Tetrahedron, 47, 5051 (1991).
88. Y. Ogata and K. Tanaka, Can. J. Chem., 59, 718 (1981).
89. T. Q. Dinh, X. Du, C. D. Smith, and R. W. Armstrong, J. Org. Chem., 62, 6773 (1997).
90. The reaction of chiral aliphatic nitrones with ketene silyl acetals: a) Y. Kita, F. Itoh, O. Tamura, Y. Y. Ke, and Y. Tamura, Tetrahedron Lett., 28, 1431 (1987).
91. b) P. Merino, S. Franco, F. L. Merchan, and T. Tejero, Tetrahedron Lett., 39, 6411 (1998).
92. c) S. Jost, Y. Gimbert, A. E. Greene, and F. Fotiadu, J. Org. Chem., 62, 6672 (1997).
93. S. C. Mayer, J. Ramanjulu, M. D. Vera, A. J. Pfizenmayer, and M. M. Joullié, J. Org. Chem., 59, 5192 (1994).
94. a) J.-N. Denis, S. Tchertchian, A. Tomassini, and Y. Vallée, Tetrahedron Lett., 38, 5503 (1997).
95. b) P. Merino, E. Castillo, S. Franco, F. L. Merchan, and T. Tejero, Tetrahedron: Asymmetry, 9, 1759 (1998).
96. c) P. Merino, S. Franco, F. L. Merchan, and T. Tejero, J. Org. Chem., 63, 5627 (1998).
97. a) Y. Imada, M. Yuasa, I. Nakamura, and S.-I. Murahashi, J. Org. Chem., 59, 2282 (1994).
98. b) D. Enders and J. Schankat, Helv. Chim. Acta, 78, 970 (1995).
99. c) J.-N. Denis, S. Tchertchian, A. Tomassini, and Y. Vallee, Tetrahedron Lett., 38, 5503 (1997).
100. d) M. A. Huffman, N. Yasuda, A. E. DeCamp, and E. J. J. Grabowski, J. Org. Chem., 60, 1590 (1995).
101. e) A. G. Myers, N. J. Tom, M. E. Fraley, S. B. Cohen, and D. J. Madar, J. Am. Chem. Soc., 119, 6072 (1997).
102. f) S. N. Osipov, A. S. Golubev, N. Sewald, and K. Burger, Tetrahedron Lett., 34, 5965 (1997).
103. M. Hashimoto, Y. Eda, Y. Osanai, T. Iwai, and S. Aoki, Chem. Lett., 1986, 893.
104. D. H. R. Barton, Y. Herve, P. Potier, and J. Thierry, J. Chem. Soc., Chem. Commun., 1984, 1298.
105. A. Goti, S. Cicchi, V. Fedi, L. Nannelli, and A. Brandi, J. Org. Chem., 62, 3119 (1997).
106. A. Bernardi, F. Micheli, D. Potenza, C. Scolastico, and R. Villa, Tetrahedron Lett., 31, 4949 (1990).
107. a) S. Shatzmiller, B.-Z. Dolithzky, and E. Bahar, Liebigs Ann. Chem., 1991, 375.
108. b) V. W. Magaard, R. M. Sanchez, J. W. Bean, and M. L. Moore, Tetrahedron Lett., 34, 381 (1993).
109. c) F. L. Merchan, P. Merino, and T. Tejero, Tetrahedron Lett., 36, 6949 (1995).
110. T. A. Geissman and A. C. Waiss, Jr., J. Org. Chem., 27, 139 (1962).
111. Enantioselective syntheses of the Geissman-Waiss lactone: a) J. Buchanan, G. Singh, and R. Wightman, J. Chem. Soc., Chem. Commun., 1984, 1299.
112. b) H. Rüeger and M. Benn, Heterocycles, 19, 23 (1982).
113. c) N. Ikota and A. Hanaki, Heterocycles., 27, 2535 (1988).
114. d) K. Shishido, Y. Sukegawa, and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1987, 993.
115. e) M. Thaning and L. Wistrand, J. Org. Chem., 55, 1406 (1990).
116. f) H. Takahata, Y. Banba, and T. Momose, Tetrahedron: Asymmetry, 2, 445 (1991).
117. E. Buehler, J. Org. Chem., 32, 261 (1967).
118. T. Yakura, M. Nakazawa, T. Takino, and M. Ikeda, Chem. Pharm. Bull., 40, 2014 (1992).
119. M. J. Fray, R. H. Jones, and E. J. Thomas, J. Chem. Soc., Perkin Trans. 1, 1985, 2753.
120. F. Orsini, F. Pelizzoni, M. Sisti, and L. Verotta, Org. Prep. Proced. Int., 21, 505 (1989).