Stereoselective and enantioselective synthesis of new fluoroalkyl peptidomimetic units: Amino alcohols and isoserines

ACS Symposium Series

Volumn 746, Issue , 1999, Pages 84-97

  Abouabdellah, Ahmed ^a   Bégué, Jean Pierre ^a   Bonnet Delpon, Danièle ^a   Kornilov, Andrei ^a   Rodrigues, Isabelle ^a   Thanh Nga, Truong Thi ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042411296     PISSN: 00976156     EISSN: None     Source Type: Book Series    
DOI: None     Document Type: Article

References (84)

1. Grayson, M. Ed. Kirk-Othmer Encycl. Chem. Techno. 1982, 17, 311-345.
2. Tomioka, K. Synthesis 1990, 541; Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 50, 49-68.
3. Tomioka, K. Synthesis 1990, 541; Noyori, R.; Kitamura, M. Angew. Chem. Int. Ed. Engl. 1991, 50, 49-68.
4. Marti, R.E.; Heinzer, J.; Seebach, D. Liebigs Ann. 1995, 1193-1215.
5. Bravo, P.; Farina, A.; Kukhar, V.; Markosky, A.; Meille, S.; Soloshonok, V.; Sorochinsky; A.; Viani, F.; Zanda, M.; Zappala, C. J. Org. Chem. 1997, 62, 3424-3425.
6. Tanaka, K.; Ishiguro, Y.; Mitsuhashi, K. Bull. Chem. Soc. Jpn 1993, 66, 661-663. Uneyama, K.; Hao, J.; Amii, H. Tetrahedron Lett. 1998, 39, 4079-4082.
7. Tanaka, K.; Ishiguro, Y.; Mitsuhashi, K. Bull. Chem. Soc. Jpn 1993, 66, 661-663. Uneyama, K.; Hao, J.; Amii, H. Tetrahedron Lett. 1998, 39, 4079-4082.
8. Imperiali, B. Synthetic Peptides in Biotechnology, A. R. Liss, Inc. 1988, 97-129.
9. Imperiali, B.; Abeles, R.B. Biochemistry 1985, 24, 1813-1817; Imperiali, B.; Abeles, R.B. Biochemistry 1986, 25, 3760-3767.
10. Imperiali, B.; Abeles, R.B. Biochemistry 1985, 24, 1813-1817; Imperiali, B.; Abeles, R.B. Biochemistry 1986, 25, 3760-3767.
11. Brady, K.; Liang, T.C.; Abeles, R.H. Biochemistry 1989, 28, 9066-9070; Liang, T.C.; Abeles, R.H. Biochemistry 1987, 26, 7603-7608; Brady, K.; Wei, A.; Ringe, D.; Abeles, R.H. Biochemistry 1990, 29, 7600-7607; Brady, K.; Abeles, R.H. Biochemistry 1990, 29, 7608-7617.
12. Brady, K.; Liang, T.C.; Abeles, R.H. Biochemistry 1989, 28, 9066-9070; Liang, T.C.; Abeles, R.H. Biochemistry 1987, 26, 7603-7608; Brady, K.; Wei, A.; Ringe, D.; Abeles, R.H. Biochemistry 1990, 29, 7600-7607; Brady, K.; Abeles, R.H. Biochemistry 1990, 29, 7608-7617.
13. Brady, K.; Liang, T.C.; Abeles, R.H. Biochemistry 1989, 28, 9066-9070; Liang, T.C.; Abeles, R.H. Biochemistry 1987, 26, 7603-7608; Brady, K.; Wei, A.; Ringe, D.; Abeles, R.H. Biochemistry 1990, 29, 7600-7607; Brady, K.; Abeles, R.H. Biochemistry 1990, 29, 7608-7617.
14. Brady, K.; Liang, T.C.; Abeles, R.H. Biochemistry 1989, 28, 9066-9070; Liang, T.C.; Abeles, R.H. Biochemistry 1987, 26, 7603-7608; Brady, K.; Wei, A.; Ringe, D.; Abeles, R.H. Biochemistry 1990, 29, 7600-7607; Brady, K.; Abeles, R.H. Biochemistry 1990, 29, 7608-7617.
15. (a) Dunlap, R.P.; Stone, P.J.; Abeles, R.H. Biochem. Biophys. Res. Commun. 1987, 145, 509-513;
16. (b) Stein, R.L.; Strimpler, A.M.; Edwards, P.D., Lewis, J.J.; Mauger, R.C.; Schwartz, J.A.; Stein, M.M.; Trainor, D.A.; Wildonger, R.A.; Zottola, M.A. Biochemistry 1987, 26, 2682-2689;
17. (c) Govardhan, C.P.; Abeles, R.H. Arch. Biochem. Biophys. 1990, 280, 137-146;
18. (d) Warner, P.; Green, R.C.; Gomes, B.; Strimpler, A.M. J. Med. Chem. 1994, 37, 3090-3099;
19. (e) Berstein, P.R.; Gomes, B.C.; Kosmider, B.J.; Vacek, E.P.; Williams, J.C. J. Med. Chem. 1995, 38, 212-215;
20. (f) Veale, C.A.; Damewood, J.R.; Steelman, G.B.; Bryant, C., Gomes, B.; Williams, J. Med. Chem. 1995, 38, 86-97;
21. (g) Brown, F.J.; Andisik, D.W.; Berstein, P.R.; Bryant, C.B.; Ceccarelli, C.; Damewood, J.R.; Edwards, P.D.; Earley, R.A.; Feeney, S.; Green, R.C.; Gomes, B.; Kosmider, B.J.; Krell, R.D.; Shaw, A.; Steelman, G.B.; Thomas, R.M.; Vacek, E.P.; Veale, C.A.; Tuthill, P.A.; Warner, P.; Williams, J.C.; Wolanin, D.J.; Woolson, S.A. J. Med. Chem. 1994, 37, 1259-1261.
22. (a) Peet, N.P.; Burkhart, J.P.; Angelastro, M.R.; Giroux, E.L.; Mehdi, S.; Bey, P.; Kolb, M.; Neises, B.; Schirlin, D. J. Med. Chem. 1990, 33, 394-407;
23. (b) Skiles, J.W.; Fuchs, V.; Miao, C.; Sorcek, R.; Grozinger, K.G.; Mauldin, S.C.; Vitous, J.; Mui, P.W.; Jacober, S.; Chow, G.; Matteo, M.; Skoog, M.; Weldon, S.M.; Possanza, G.; Keirns, J.; Letts, G.; Rosenthal, A.S. J. Med. Chem. 1992, 35, 641-662;
24. (c) Angelastro, M.R., Baugh, L.E.; Bey, P.; Burkhart, J.P.; Chen, T.M.; Durham, S.L.; Hare, C.M.; Huber, E.W.; Janusz, M.J.; Koehl, J.R.; Marquart, A.L.; Mehdi, S.; Peet, N.P. J. Med. Chem. 1994, 37, 4538-4554.
25. Ueda, T.; Kam, C.M.; Powers, J.C. Biochem. J. 1990, 265, 539-545.
26. Neises, B.; Ganzhorn, A. Eur. Pat. Appl. EP 503,203, 1992; Chem. Abstract 1993, 118, 148063y.
27. (a) Sham, H.L.; Stein, H.; Rempel, C.A.; Cohen, J.; Plattner, J.J. FEBS Lett. 1987, 220, 299-301;
28. (b) Tarnus, C.; Jung, M.J.; Rémy, J.M.; Baltzer, S.; Schirlin, D. FEBS Lett. 1989, 249, 47-50;
29. (c) Thaisrivongs, S.; Pals, D.T.; Turner, S.R. in Selective Fluorination in Organic and Bioorganic Chemistry, J. T. Welch Ed., ACS Symposium Series 456, Washington D.C. 1991, pp 164-173.
30. Patel, D.V.; Rielly-Gauvin, K.; Ryono, D.E. Tetrahedron Lett. 1988, 29, 4665-4668; Patel, D.V.; Rielly-Gauvin, K.; Ryono, D.E.; Free, C.A.; Smith, S.A.; Petrillo Jr, E.W. J. Med. Chem. 1993, 36, 2431-2447.
31. Patel, D.V.; Rielly-Gauvin, K.; Ryono, D.E. Tetrahedron Lett. 1988, 29, 4665-4668; Patel, D.V.; Rielly-Gauvin, K.; Ryono, D.E.; Free, C.A.; Smith, S.A.; Petrillo Jr, E.W. J. Med. Chem. 1993, 36, 2431-2447.
32. (a) Giordano, C.; Gallina, C.; Consalvi, V.; Scandurra, R. Eur. J. Med. Chem. 1989, 24, 357-362;
33. (b) Smith, R.A.; Copp, L.J.; Donnelly, S.L.; Spencer, R.W.; Krantz, A. Biochemistry 1988, 27, 6568-6573.
34. (a) Bergeson, S.H.; Schwartz, J.A.; Stein, M.M.; Wildonger, R.A.; Edwards, P.D.; Shaw, A; Trainor, D.A.; Wolanin, D.J. U.S. Pat. 4,910,190; 1990;
35. (b) Chem. Abstr. 1991, 114, 120085m.
36. (c) Edwards, P.D. Tetrahedron Lett. 1992, 33, 4279-4282.
37. (d) Kolb, M.; Neises, B. Tetrahedron Lett. 1986, 27, 4437-4440;
38. (d) Walter, M.W.; Adlington, R.M.; Baldwin, J.E.; Schofield C.J. J. Org. Chem. 1998, 63, 5179-5179.
39. Imperiali, B.; Abeles, R.H. Tetrahedron Lett. 1986, 27, 135-138; Kolb, M.; Barth, J.; Neises, B. Tetrahedron Lett. 1986, 27, 1579-1582; Kolb, M.; Neises, B.; Gerhart, F. Liebigs Ann. Chem. 1990, 1-6.
40. Imperiali, B.; Abeles, R.H. Tetrahedron Lett. 1986, 27, 135-138; Kolb, M.; Barth, J.; Neises, B. Tetrahedron Lett. 1986, 27, 1579-1582; Kolb, M.; Neises, B.; Gerhart, F. Liebigs Ann. Chem. 1990, 1-6.
41. Imperiali, B.; Abeles, R.H. Tetrahedron Lett. 1986, 27, 135-138; Kolb, M.; Barth, J.; Neises, B. Tetrahedron Lett. 1986, 27, 1579-1582; Kolb, M.; Neises, B.; Gerhart, F. Liebigs Ann. Chem. 1990, 1-6.
42. (a) Bégué, J.P.; Bonnet-Delpon, D.; Sdassi, H. Tetrahedron Lett. 1992, 33, 1879-1882.
43. (b) Abouabdellah, A.; Bégué, J.P.; Bonnet-Delpon, D.; Rodriguez, I.; Kornilov, A.; Richard, C. J. Org. Chem. 1998, 63, 6529.
44. Bégué, J.P.; Bonnet-Delpon, D.; Fischer-Durand N.; Reboud-Raveaux, M.; Amour, A. Tetrahedron: Asymmetry 1994, 5, 1099-1110.
45. Bégué, J.P.; Mesureur, D. J. Fluorine Chem. 1988, 39, 271; Bégué, J.P.; Bonnet-Delpon, D.; Née, G.; Wu, S.W. J. Org. Chem. 1992, 57, 3807.
46. Bégué, J.P.; Mesureur, D. J. Fluorine Chem. 1988, 39, 271; Bégué, J.P.; Bonnet-Delpon, D.; Née, G.; Wu, S.W. J. Org. Chem. 1992, 57, 3807.
47. Bégué, J.P.; Bonnet-Delpon, D.; Kornilov, A. Organic Synth. 1998, 75, 153-160.
48. Bégué, J.P.; Benayoud, F.; Bonnet-Delpon, D.; Fischer-Durand, N.; Sdassi, H. Synthesis, 1993, 1083-1085.
49. Bégué, J.P.; Bonnet-Delpon, D. in Biomedical Frontiers of Fluorine Chemistry, ACS symposium Series, vol. 639, Ojima, I.; McCarthy, J.R.; Welch, J.T. Eds, Washington DC, Chapter 4, 1996, pp 59-72.
50. Bégue, J.P.; Bonnet-Delpon, D.; Kornilov, A. Synthesis 1996, 529-531.
51. (a) Levin, J.I.; Turos, S.M.; Weinreb S.M. Synth. Commun. 1982, 12, 989-993;
52. (b) Overman, L.E. Flippin, L.A. Tetrahedron Lett. 1981, 22, 195-198.
53. Bégué, J.P.; Bonnet-Delpon, D.; Benayoud, F. J. Org. Chem. 1995, 60, 5029-5036.
54. Sham, H.L.; Trempel, C.A.; Stein, H.; Cohen, J.J. J. Chem. Soc. Chem. Comm. 1990, 904-905.
55. Jacobsen, E.N.; Zhang, W.; Muci, A.R.; Ecker, J.R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063-7064.
56. Brandies, B.D.; Jacobsen, E.N. J. Org. Chem. 1994, 59, 4378-4380.
57. Katsuki, T. J. Synth. Org. Chem. Jpn 1995, 53, 940-951.
58. Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389-4392.
59. Adam, W.; Fell, R.T.; Mock-Knoblauch, C.; Saha-Möller, C. Tetrahedron Lett. 1996, 37, 4389-4392.
60. Ojima, I.; Kato, K.; Jameison, F.A.; Conway, J. Bioorganic Med. Chem. Lett. 1992, 2, 219-222.
61. Schirlin, D.; Tarnus, C.; Baltzer, S.; Rémy, J.M. Bioorg. Med. Chem. Lett. 1992, 2, 651-654.
62. Rich, D.H. J. Med. Chem. 1985, 28, 263. Moore, M.L.; Dreyer, G.B. Perspect. Drug Dis. Design 1993, 1, 85-108. Gait, M.J.; Kam, J. TIBTECH, 1995, 13, 430-437.
63. Rich, D.H. J. Med. Chem. 1985, 28, 263. Moore, M.L.; Dreyer, G.B. Perspect. Drug Dis. Design 1993, 1, 85-108. Gait, M.J.; Kam, J. TIBTECH, 1995, 13, 430-437.
64. Rich, D.H. J. Med. Chem. 1985, 28, 263. Moore, M.L.; Dreyer, G.B. Perspect. Drug Dis. Design 1993, 1, 85-108. Gait, M.J.; Kam, J. TIBTECH, 1995, 13, 430-437.
65. (a) Georg, G.I.; Ravikumar, V.T. In The Organic Chemistry of β-Lactams; Georg, G.I. Ed.; VCH Publishers: New York, 1992, pp 295-368 and references cited therein.
66. (b) Ojima, I. In The Organic Chemistry of β-Lactams; Georg, G.I. Ed.; VCH Publishers: New York, 1992, pp 197-255.
67. Quanti, G.; Banfi, L.; Narisano, E; Scolastico, C.; Bosone, E. Synthesis 1985, 609-611.
68. Kaneko, S.; Yamazaki, T.; Kitazume, T. J. Org. Chem. 1993, 58, 2302-2312.
69. Browne, M.; Burnett, D.A.; Caplen, M.A.; Chen, L.Y.; Clader, J.W.; Domalsky, M.; Dugar, S.; Pushpavanam, P.; Sher, R.; Vaccaro, W.; Zhao, H. Tetrahedron Lett. 1995, 36, 2555-2558.
70. Palomo, C.; Aizpurua, J.M.; Galarza, R.; Mielgo, A. J. Chem. Soc. Chem. Comm. 1996, 633-634.
71. Ojima, I.; Slater, J.C. Pera, P.; Veith, J.M.; Abouabdellah, A.; Bégué, J.P.; Bernacki, R.J. Bioorganic Med. Chem. Lett. 1997, 7, 133-138.
72. Ojima, I.; Kuduk, S.D.; Slater, J.C.; Gimi, R.H.; Sun, C.M.; Chabravarty, S.; Ourevitch, M.; Abouabdellah, A.; Bonnet-Delpon, D.; Bégué, J.P.; Veith, J.M.; Pera, P.; Bernacki, R.J. chapter 17 in "Biomedical Frontiers of Fluorine Chemistry", Ojima, I.; McCarthy, J.R.; Welch, J.T. Ed.; A.C.S.: Washington, D.C. 1996, pp 228-245.
73. For reviews, Hart, D.J.; Ha, D.C. Chem. Rev. 1989, 89, 1447; Ojima, I. Account Chem. Res. 1995, 28, 383-389 and references cited herein.
74. For reviews, Hart, D.J.; Ha, D.C. Chem. Rev. 1989, 89, 1447; Ojima, I. Account Chem. Res. 1995, 28, 383-389 and references cited herein.
75. (a) Ojima, I.; Habus, I. Tetrahedron Lett. 1990, 46, 3841.
76. (b) Georg, G.I.; Kant, J.; Gill, H.S. J. Am. Chem. Soc. 1987, 109, 1129.
77. (a) Ojima, I.; Habus, I.; Zhao, M.; Zucco, M.; Park, Y.H.; Sun, C.M.; Brigaud, T. Tetrahedron 1992, 48, 6985-7012.
78. (b) Ojima, I.; Habus, I.; Zhao, M.; Georg, G.I.; Jayasinghe, L.R. J. Org. Chem. 1991, 56, 1681-1683.
79. Ojima, I.; Park, Y.H.; Sun, C.M.; Brigaud, T.; Zhao, M. Tetrahedron Lett. 1992, 33, 5737-5740.
80. Abouabdellah, A.; Bégué, J.P.; Bonnet-Delpon, D. Synlett 1996, 399-400. Abouabdellah, A.; Bégué, J.P.; Bonnet-Delpon, D.; T. T. Thanh Nga J. Org. Chem. 1997, 62, 8826-8833; ibidem 1998, 63, 5294.
81. Abouabdellah, A.; Bégué, J.P.; Bonnet-Delpon, D. Synlett 1996, 399-400. Abouabdellah, A.; Bégué, J.P.; Bonnet-Delpon, D.; T. T. Thanh Nga J. Org. Chem. 1997, 62, 8826-8833; ibidem 1998, 63, 5294.
82. Abouabdellah, A.; Bégué, J.P.; Bonnet-Delpon, D. Synlett 1996, 399-400. Abouabdellah, A.; Bégué, J.P.; Bonnet-Delpon, D.; T. T. Thanh Nga J. Org. Chem. 1997, 62, 8826-8833; ibidem 1998, 63, 5294.
83. Hashimoto, Y.; Kai, A.; Saigo, K. Tetrahedron Lett. 1995, 48, 8821-8824. Georg, G.I.; Wu, Z. Tetrahedron Lett. 1994, 47, 381-384.
84. Hashimoto, Y.; Kai, A.; Saigo, K. Tetrahedron Lett. 1995, 48, 8821-8824. Georg, G.I.; Wu, Z. Tetrahedron Lett. 1994, 47, 381-384.