Synthesis of a boronic acid analogue of L-ornithine

Synthesis

Volumn , Issue 11, 1996, Pages 1371-1374

  Lebarbier, Caroline ^a   Carreaux, François ^a   Carboni, Bertrand ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

asymmetric synthesis; homologation reaction; ornithine decarboxylase; polyamines; amino boronic acid

Indexed keywords

AMINO ACID DERIVATIVE; ORGANOBORON DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029802977     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4376     Document Type: Article

References (24)

1. For a review, see: Morin, C. Tetrahedron 1994, 50, 12521. For some more recent references, see: Thrombin inhibitor: Wityak, J.; Earl, R. A.; Abelman, M. M.; Bethel, Y.B.; Fisher, B.N.; Kauffman, G.S.; Kettner, C.A.; Ma, P.; McMillan, J. L.; Mersinger, L. J.; Pesti, J.; Pierce, M. E.; Rankin, F.W.; Chorvat, R.J.; Confalone, P.N. J. Org. Chem. 1995, 60, 3717. Subtilisin Carlsberg and α-chimotrypsyn inhibitor: Martichonok, V.; Jones, B. J. J. Am. Chem. Soc. 1996, 118, 950. Dipeptidyl peptidase IV inhibitor: Snow, R.J.; Bachovchin, W. W.; Barton, R. W.; Campbell, S. J.; Coutts, S. J.; Freeman, D. M.; Gutheil, W. G.; Kelly, T. A.; Kennedy, C. A.; Krolikowski, D. A.; Leonard, S. F.; Pargellis, C. A.; Tong, L.; Adams, J. J. Am. Chem. Soc. 1994, 116, 10860. β-Lactamase inhibitor: Martin, R.; Jones, J. B. Tetrahedron Lett. 1995, 36, 8399.
2. For a review, see: Morin, C. Tetrahedron 1994, 50, 12521. For some more recent references, see: Thrombin inhibitor: Wityak, J.; Earl, R. A.; Abelman, M. M.; Bethel, Y.B.; Fisher, B.N.; Kauffman, G.S.; Kettner, C.A.; Ma, P.; McMillan, J. L.; Mersinger, L. J.; Pesti, J.; Pierce, M. E.; Rankin, F.W.; Chorvat, R.J.; Confalone, P.N. J. Org. Chem. 1995, 60, 3717. Subtilisin Carlsberg and α-chimotrypsyn inhibitor: Martichonok, V.; Jones, B. J. J. Am. Chem. Soc. 1996, 118, 950. Dipeptidyl peptidase IV inhibitor: Snow, R.J.; Bachovchin, W. W.; Barton, R. W.; Campbell, S. J.; Coutts, S. J.; Freeman, D. M.; Gutheil, W. G.; Kelly, T. A.; Kennedy, C. A.; Krolikowski, D. A.; Leonard, S. F.; Pargellis, C. A.; Tong, L.; Adams, J. J. Am. Chem. Soc. 1994, 116, 10860. β-Lactamase inhibitor: Martin, R.; Jones, J. B. Tetrahedron Lett. 1995, 36, 8399.
3. For a review, see: Morin, C. Tetrahedron 1994, 50, 12521. For some more recent references, see: Thrombin inhibitor: Wityak, J.; Earl, R. A.; Abelman, M. M.; Bethel, Y.B.; Fisher, B.N.; Kauffman, G.S.; Kettner, C.A.; Ma, P.; McMillan, J. L.; Mersinger, L. J.; Pesti, J.; Pierce, M. E.; Rankin, F.W.; Chorvat, R.J.; Confalone, P.N. J. Org. Chem. 1995, 60, 3717. Subtilisin Carlsberg and α-chimotrypsyn inhibitor: Martichonok, V.; Jones, B. J. J. Am. Chem. Soc. 1996, 118, 950. Dipeptidyl peptidase IV inhibitor: Snow, R.J.; Bachovchin, W. W.; Barton, R. W.; Campbell, S. J.; Coutts, S. J.; Freeman, D. M.; Gutheil, W. G.; Kelly, T. A.; Kennedy, C. A.; Krolikowski, D. A.; Leonard, S. F.; Pargellis, C. A.; Tong, L.; Adams, J. J. Am. Chem. Soc. 1994, 116, 10860. β-Lactamase inhibitor: Martin, R.; Jones, J. B. Tetrahedron Lett. 1995, 36, 8399.
4. For a review, see: Morin, C. Tetrahedron 1994, 50, 12521. For some more recent references, see: Thrombin inhibitor: Wityak, J.; Earl, R. A.; Abelman, M. M.; Bethel, Y.B.; Fisher, B.N.; Kauffman, G.S.; Kettner, C.A.; Ma, P.; McMillan, J. L.; Mersinger, L. J.; Pesti, J.; Pierce, M. E.; Rankin, F.W.; Chorvat, R.J.; Confalone, P.N. J. Org. Chem. 1995, 60, 3717. Subtilisin Carlsberg and α-chimotrypsyn inhibitor: Martichonok, V.; Jones, B. J. J. Am. Chem. Soc. 1996, 118, 950. Dipeptidyl peptidase IV inhibitor: Snow, R.J.; Bachovchin, W. W.; Barton, R. W.; Campbell, S. J.; Coutts, S. J.; Freeman, D. M.; Gutheil, W. G.; Kelly, T. A.; Kennedy, C. A.; Krolikowski, D. A.; Leonard, S. F.; Pargellis, C. A.; Tong, L.; Adams, J. J. Am. Chem. Soc. 1994, 116, 10860. β-Lactamase inhibitor: Martin, R.; Jones, J. B. Tetrahedron Lett. 1995, 36, 8399.
5. For a review, see: Morin, C. Tetrahedron 1994, 50, 12521. For some more recent references, see: Thrombin inhibitor: Wityak, J.; Earl, R. A.; Abelman, M. M.; Bethel, Y.B.; Fisher, B.N.; Kauffman, G.S.; Kettner, C.A.; Ma, P.; McMillan, J. L.; Mersinger, L. J.; Pesti, J.; Pierce, M. E.; Rankin, F.W.; Chorvat, R.J.; Confalone, P.N. J. Org. Chem. 1995, 60, 3717. Subtilisin Carlsberg and α-chimotrypsyn inhibitor: Martichonok, V.; Jones, B. J. J. Am. Chem. Soc. 1996, 118, 950. Dipeptidyl peptidase IV inhibitor: Snow, R.J.; Bachovchin, W. W.; Barton, R. W.; Campbell, S. J.; Coutts, S. J.; Freeman, D. M.; Gutheil, W. G.; Kelly, T. A.; Kennedy, C. A.; Krolikowski, D. A.; Leonard, S. F.; Pargellis, C. A.; Tong, L.; Adams, J. J. Am. Chem. Soc. 1994, 116, 10860. β-Lactamase inhibitor: Martin, R.; Jones, J. B. Tetrahedron Lett. 1995, 36, 8399.
6. Deadman, J. J.; Elgendy, S.; Goodwin, C. A.; Green, D.; Baban, J. A.; Patel, G.; Skordalakes, E.; Chino, N.; Claeson, G.; Kakkar, V. V.; Scully, M F. J. Med. Chem. 1995, 38, 1511 and references therein
7. Duncan, K.; Faraci, W. S.; Matteson, D. S.; Walsh, C. T. Biochemistry 1989, 28, 3541
8. Khoukhi, M.; Vaultier, M.; Benalil, A.; Carboni, B. Synthesis 1996, in press. Carboni, B.; Benalil, A.; Vaultier, M. J. Org. Chem. 1993, 58, 3736 and references therein.
9. Khoukhi, M.; Vaultier, M.; Benalil, A.; Carboni, B. Synthesis 1996, in press. Carboni, B.; Benalil, A.; Vaultier, M. J. Org. Chem. 1993, 58, 3736 and references therein.
10. Jego, J. M.; Carboni, B.; Vaultier, M. J. Organomet. Chem. 1992, 435, 1.
11. Seiler, N. In The Neuropharmacology of Polyamines; Carter, C. Ed.; Academic: London, 1994, p 1. For other leading references on polyamines, see: Inhibition of Polyamine Metabolism; Mc Cann, P. P.; Pegg, A. E.; Sjoerdsma, A. Eds.; Academic: San Diego, 1987. The Physiology of Polyamines; Bachrach, U.; Heimer, Y. M. Eds.; CRC Press: Boca Raton, Florida, 1989, Vol. 1 and 2. Les Polyamines; Moulinoux, J. P.; Quemener, V., Eds.; Médecine Sciences: Flammarion, Paris, 1991.
12. Seiler, N. In The Neuropharmacology of Polyamines; Carter, C. Ed.; Academic: London, 1994, p 1. For other leading references on polyamines, see: Inhibition of Polyamine Metabolism; Mc Cann, P. P.; Pegg, A. E.; Sjoerdsma, A. Eds.; Academic: San Diego, 1987. The Physiology of Polyamines; Bachrach, U.; Heimer, Y. M. Eds.; CRC Press: Boca Raton, Florida, 1989, Vol. 1 and 2. Les Polyamines; Moulinoux, J. P.; Quemener, V., Eds.; Médecine Sciences: Flammarion, Paris, 1991.
13. Seiler, N. In The Neuropharmacology of Polyamines; Carter, C. Ed.; Academic: London, 1994, p 1. For other leading references on polyamines, see: Inhibition of Polyamine Metabolism; Mc Cann, P. P.; Pegg, A. E.; Sjoerdsma, A. Eds.; Academic: San Diego, 1987. The Physiology of Polyamines; Bachrach, U.; Heimer, Y. M. Eds.; CRC Press: Boca Raton, Florida, 1989, Vol. 1 and 2. Les Polyamines; Moulinoux, J. P.; Quemener, V., Eds.; Médecine Sciences: Flammarion, Paris, 1991.
14. Seiler, N. In The Neuropharmacology of Polyamines; Carter, C. Ed.; Academic: London, 1994, p 1. For other leading references on polyamines, see: Inhibition of Polyamine Metabolism; Mc Cann, P. P.; Pegg, A. E.; Sjoerdsma, A. Eds.; Academic: San Diego, 1987. The Physiology of Polyamines; Bachrach, U.; Heimer, Y. M. Eds.; CRC Press: Boca Raton, Florida, 1989, Vol. 1 and 2. Les Polyamines; Moulinoux, J. P.; Quemener, V., Eds.; Médecine Sciences: Flammarion, Paris, 1991.
15. Matteson, D.S. Stereodirected Synthesis with Organoboranes; Springer: Berlin, 1995, p 196.
16. Jego, J. M.; Carboni, B.; Vaultier, M. Bull. Soc. Chim. Fr. 1992, 129, 554.
17. Brown, H. C.; Singh, S. M.; Rangaishenvi, M. V. J. Org. Chem. 1986, 51, 3150.
18. 1H NMR spectrum of the crude homologated boronic ester (different chemical shift of one of the pinanyl protons that appears as a doublet near δ = 1.10-1.15. See for example: Matteson, D.S.; Sadhu, K. M.; Peterson, M.L. J. Am. Chem. Soc. 1986, 108, 810. In our hands, we observed that it was quite difficult to measure the diastereomeric purity with a good precision.
19. This method was generalized to other α-chloro boronic esters. Ollivault, M.; Monnier, L.; Carboni, B. manuscript in preparation.
20. 3 (334.2): C, 57.50; H, 8.14; N, 16.76; found: C, 57.4; H, 8.3; N, 16.9.
21. This sequence was realized with a racemic α-chloro boronic ester.
22. Similar decomposition of α-amino boronic acids or esters have been already reported: Matteson, D. S.; Sadhu, K. M. Organometallics 1984, 3, 614.
23. Shaw, K. J.; Luly, J. R.; Rapoport, H. J. Org. Chem. 1985, 50, 4515.
24. Matteson, D. S.; Jesthi, P. K.; Sadhu, K. M. Organometallics 1984, 3, 1284.