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Volumn 10, Issue 11, 1999, Pages 2113-2118

An efficient synthesis of (R)-(-)-baclofen

Author keywords

[No Author keywords available]

Indexed keywords

BACLOFEN; BACLON; CYCLOBUTANONE DERIVATIVE; KETENE DERIVATIVE; PROTON; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033522736     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00235-9     Document Type: Article
Times cited : (42)

References (39)
  • 1
    • 0002565192 scopus 로고    scopus 로고
    • In Neurotransmission and The Central Nervous System;
    • Hardman, J. E.; Limbird, L. E.; Molinoff, P. E.; Ruddon, R. W.; Gilman, A. G., Eds.; McGraw-Hill: New York
    • Bloom, F. E. In Neurotransmission and The Central Nervous System; Hardman, J. E.; Limbird, L. E.; Molinoff, P. E.; Ruddon, R. W.; Gilman, A. G., Eds.; Goodman & Gilman's The Pharmacological Basis of Therapeutics, 9th ed.; McGraw-Hill: New York, 1996; pp. 267-282.
    • (1996) Goodman & Gilman's the Pharmacological Basis of Therapeutics, 9th Ed.; , pp. 267-282
    • Bloom, F.E.1
  • 3
    • 0023804944 scopus 로고
    • (b)
    • (b) Nicoll, R. A. Science 1988, 241, 545-551;
    • (1988) Science , vol.241 , pp. 545-551
    • Nicoll, R.A.1
  • 9
    • 0002246124 scopus 로고
    • Benzodiazepine/GABA receptors and chloride channels
    • Olsen, R. W.; Veuter, J. C., Eds.; A. R. Liss: New York
    • Johnston, G. A. R. Benzodiazepine/GABA receptors and chloride channels. In Receptor Biochemistry and Methodology; Olsen, R. W.; Veuter, J. C., Eds.; A. R. Liss: New York, 1986; Vol. 5, pp. 57-71.
    • (1986) In Receptor Biochemistry and Methodology; , vol.5 , pp. 57-71
    • Johnston, G.A.R.1
  • 14
    • 4243910033 scopus 로고
    • For some examples of the racemic synthesis of baclofen and derivatives see: (a) Swiss Patent 499,046
    • For some examples of the racemic synthesis of baclofen and derivatives see: (a) Kerberle, H.; Faigle, J. W.; Wilhelm, M. Swiss Patent 499,046, Chem. Abstr. 1968, 69, 106273f; (b) Wall, G. M.; Baker, J. K. J. Med. Chem. 1989, 32, 1340-1348; (c) Pifferi, G.; Nizzola, R.; Cristoni, A. Il Farmaco 1994, 49, 453-455; Chem. Abstr. 1995, 122, 204918; (d) Ibuka, T.; Schoenfelder, A.; Bildstein, P.; Mann, A. Synth. Commun. 1995, 25, 1777-1782.
    • (1968) Chem. Abstr. , vol.69
    • Kerberle, H.1    Faigle, J.W.2    Wilhelm, M.3
  • 15
    • 0024356397 scopus 로고
    • (b)
    • For some examples of the racemic synthesis of baclofen and derivatives see: (a) Kerberle, H.; Faigle, J. W.; Wilhelm, M. Swiss Patent 499,046, Chem. Abstr. 1968, 69, 106273f; (b) Wall, G. M.; Baker, J. K. J. Med. Chem. 1989, 32, 1340-1348; (c) Pifferi, G.; Nizzola, R.; Cristoni, A. Il Farmaco 1994, 49, 453-455; Chem. Abstr. 1995, 122, 204918; (d) Ibuka, T.; Schoenfelder, A.; Bildstein, P.; Mann, A. Synth. Commun. 1995, 25, 1777-1782.
    • (1989) J. Med. Chem. , vol.32 , pp. 1340-1348
    • Wall, G.M.1    Baker, J.K.2
  • 16
    • 0028074369 scopus 로고
    • (c)
    • For some examples of the racemic synthesis of baclofen and derivatives see: (a) Kerberle, H.; Faigle, J. W.; Wilhelm, M. Swiss Patent 499,046, Chem. Abstr. 1968, 69, 106273f; (b) Wall, G. M.; Baker, J. K. J. Med. Chem. 1989, 32, 1340-1348; (c) Pifferi, G.; Nizzola, R.; Cristoni, A. Il Farmaco 1994, 49, 453-455; Chem. Abstr. 1995, 122, 204918; (d) Ibuka, T.; Schoenfelder, A.; Bildstein, P.; Mann, A. Synth. Commun. 1995, 25, 1777-1782.
    • (1994) Il Farmaco , vol.49 , pp. 453-455
    • Pifferi, G.1    Nizzola, R.2    Cristoni, A.3
  • 17
    • 0345307448 scopus 로고
    • For some examples of the racemic synthesis of baclofen and derivatives see: (a) Kerberle, H.; Faigle, J. W.; Wilhelm, M. Swiss Patent 499,046, Chem. Abstr. 1968, 69, 106273f; (b) Wall, G. M.; Baker, J. K. J. Med. Chem. 1989, 32, 1340-1348; (c) Pifferi, G.; Nizzola, R.; Cristoni, A. Il Farmaco 1994, 49, 453-455; Chem. Abstr. 1995, 122, 204918; (d) Ibuka, T.; Schoenfelder, A.; Bildstein, P.; Mann, A. Synth. Commun. 1995, 25, 1777-1782.
    • (1995) Chem. Abstr. , vol.122 , pp. 204918
  • 18
    • 0028932981 scopus 로고
    • (d)
    • For some examples of the racemic synthesis of baclofen and derivatives see: (a) Kerberle, H.; Faigle, J. W.; Wilhelm, M. Swiss Patent 499,046, Chem. Abstr. 1968, 69, 106273f; (b) Wall, G. M.; Baker, J. K. J. Med. Chem. 1989, 32, 1340-1348; (c) Pifferi, G.; Nizzola, R.; Cristoni, A. Il Farmaco 1994, 49, 453-455; Chem. Abstr. 1995, 122, 204918; (d) Ibuka, T.; Schoenfelder, A.; Bildstein, P.; Mann, A. Synth. Commun. 1995, 25, 1777-1782.
    • (1995) Synth. Commun. , vol.25 , pp. 1777-1782
    • Ibuka, T.1    Schoenfelder, A.2    Bildstein, P.3    Mann, A.4
  • 19
    • 0025780986 scopus 로고
    • For some examples of the asymmetric synthesis of (-)-baclofen and derivatives see: (a)
    • For some examples of the asymmetric synthesis of (-)-baclofen and derivatives see: (a) Chênevert, R.; Desjardins, M. Tetrahedron. Lett. 1991, 32, 4249-4250; (b) Herdeis, C.; Hubmann, H. P. Tetrahedron: Asymmetry 1992, 3, 1213-1221; (c) Schoenfelder, A.; Mann, A.; Le Coz, S. Synlett 1993, 63-64; (d) Chênevert, R.; Desjardins, M. Can. J. Chem. 1994, 72, 2312-2317; (e) Prager, R. H.; Schafer, K.; Hamon, D. P. C.; Massy-Westropp, R. A. Tetrahedron 1995, 51, 11465-11472; (f) Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1302-1306; (g) Langlois, N.; Dahuron, N.; Wang, H.-S. Tetrahedron 1996, 52, 15117-15126; (h) Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 1195-1196; (i) Brenna, E.; Carraccia, N.; Fuganti, C.; Fuganti, D.; Graselli, P. Tetrahedron: Asymmetry 1997, 8, 3801-3805.
    • (1991) Tetrahedron. Lett. , vol.32 , pp. 4249-4250
    • Chênevert, R.1    Desjardins, M.2
  • 20
    • 0026646472 scopus 로고
    • (b)
    • For some examples of the asymmetric synthesis of (-)-baclofen and derivatives see: (a) Chênevert, R.; Desjardins, M. Tetrahedron. Lett. 1991, 32, 4249-4250; (b) Herdeis, C.; Hubmann, H. P. Tetrahedron: Asymmetry 1992, 3, 1213-1221; (c) Schoenfelder, A.; Mann, A.; Le Coz, S. Synlett 1993, 63-64; (d) Chênevert, R.; Desjardins, M. Can. J. Chem. 1994, 72, 2312-2317; (e) Prager, R. H.; Schafer, K.; Hamon, D. P. C.; Massy-Westropp, R. A. Tetrahedron 1995, 51, 11465-11472; (f) Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1302-1306; (g) Langlois, N.; Dahuron, N.; Wang, H.-S. Tetrahedron 1996, 52, 15117-15126; (h) Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 1195-1196; (i) Brenna, E.; Carraccia, N.; Fuganti, C.; Fuganti, D.; Graselli, P. Tetrahedron: Asymmetry 1997, 8, 3801-3805.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1213-1221
    • Herdeis, C.1    Hubmann, H.P.2
  • 21
    • 85040160485 scopus 로고
    • (c)
    • For some examples of the asymmetric synthesis of (-)-baclofen and derivatives see: (a) Chênevert, R.; Desjardins, M. Tetrahedron. Lett. 1991, 32, 4249-4250; (b) Herdeis, C.; Hubmann, H. P. Tetrahedron: Asymmetry 1992, 3, 1213-1221; (c) Schoenfelder, A.; Mann, A.; Le Coz, S. Synlett 1993, 63-64; (d) Chênevert, R.; Desjardins, M. Can. J. Chem. 1994, 72, 2312-2317; (e) Prager, R. H.; Schafer, K.; Hamon, D. P. C.; Massy-Westropp, R. A. Tetrahedron 1995, 51, 11465-11472; (f) Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1302-1306; (g) Langlois, N.; Dahuron, N.; Wang, H.-S. Tetrahedron 1996, 52, 15117-15126; (h) Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 1195-1196; (i) Brenna, E.; Carraccia, N.; Fuganti, C.; Fuganti, D.; Graselli, P. Tetrahedron: Asymmetry 1997, 8, 3801-3805.
    • (1993) Synlett , pp. 63-64
    • Schoenfelder, A.1    Mann, A.2    Le Coz, S.3
  • 22
    • 0028532754 scopus 로고
    • (d)
    • For some examples of the asymmetric synthesis of (-)-baclofen and derivatives see: (a) Chênevert, R.; Desjardins, M. Tetrahedron. Lett. 1991, 32, 4249-4250; (b) Herdeis, C.; Hubmann, H. P. Tetrahedron: Asymmetry 1992, 3, 1213-1221; (c) Schoenfelder, A.; Mann, A.; Le Coz, S. Synlett 1993, 63-64; (d) Chênevert, R.; Desjardins, M. Can. J. Chem. 1994, 72, 2312-2317; (e) Prager, R. H.; Schafer, K.; Hamon, D. P. C.; Massy-Westropp, R. A. Tetrahedron 1995, 51, 11465-11472; (f) Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1302-1306; (g) Langlois, N.; Dahuron, N.; Wang, H.-S. Tetrahedron 1996, 52, 15117-15126; (h) Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 1195-1196; (i) Brenna, E.; Carraccia, N.; Fuganti, C.; Fuganti, D.; Graselli, P. Tetrahedron: Asymmetry 1997, 8, 3801-3805.
    • (1994) Can. J. Chem. , vol.72 , pp. 2312-2317
    • Chênevert, R.1    Desjardins, M.2
  • 23
    • 0029151755 scopus 로고
    • (e)
    • For some examples of the asymmetric synthesis of (-)-baclofen and derivatives see: (a) Chênevert, R.; Desjardins, M. Tetrahedron. Lett. 1991, 32, 4249-4250; (b) Herdeis, C.; Hubmann, H. P. Tetrahedron: Asymmetry 1992, 3, 1213-1221; (c) Schoenfelder, A.; Mann, A.; Le Coz, S. Synlett 1993, 63-64; (d) Chênevert, R.; Desjardins, M. Can. J. Chem. 1994, 72, 2312-2317; (e) Prager, R. H.; Schafer, K.; Hamon, D. P. C.; Massy-Westropp, R. A. Tetrahedron 1995, 51, 11465-11472; (f) Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1302-1306; (g) Langlois, N.; Dahuron, N.; Wang, H.-S. Tetrahedron 1996, 52, 15117-15126; (h) Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 1195-1196; (i) Brenna, E.; Carraccia, N.; Fuganti, C.; Fuganti, D.; Graselli, P. Tetrahedron: Asymmetry 1997, 8, 3801-3805.
    • (1995) Tetrahedron , vol.51 , pp. 11465-11472
    • Prager, R.H.1    Schafer, K.2    Hamon, D.P.C.3    Massy-Westropp, R.A.4
  • 24
    • 0029050117 scopus 로고
    • (f)
    • For some examples of the asymmetric synthesis of (-)-baclofen and derivatives see: (a) Chênevert, R.; Desjardins, M. Tetrahedron. Lett. 1991, 32, 4249-4250; (b) Herdeis, C.; Hubmann, H. P. Tetrahedron: Asymmetry 1992, 3, 1213-1221; (c) Schoenfelder, A.; Mann, A.; Le Coz, S. Synlett 1993, 63-64; (d) Chênevert, R.; Desjardins, M. Can. J. Chem. 1994, 72, 2312-2317; (e) Prager, R. H.; Schafer, K.; Hamon, D. P. C.; Massy-Westropp, R. A. Tetrahedron 1995, 51, 11465-11472; (f) Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1302-1306; (g) Langlois, N.; Dahuron, N.; Wang, H.-S. Tetrahedron 1996, 52, 15117-15126; (h) Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 1195-1196; (i) Brenna, E.; Carraccia, N.; Fuganti, C.; Fuganti, D.; Graselli, P. Tetrahedron: Asymmetry 1997, 8, 3801-3805.
    • (1995) Chem. Pharm. Bull. , vol.43 , pp. 1302-1306
    • Yoshifuji, S.1    Kaname, M.2
  • 25
    • 0030602254 scopus 로고    scopus 로고
    • (g)
    • For some examples of the asymmetric synthesis of (-)-baclofen and derivatives see: (a) Chênevert, R.; Desjardins, M. Tetrahedron. Lett. 1991, 32, 4249-4250; (b) Herdeis, C.; Hubmann, H. P. Tetrahedron: Asymmetry 1992, 3, 1213-1221; (c) Schoenfelder, A.; Mann, A.; Le Coz, S. Synlett 1993, 63-64; (d) Chênevert, R.; Desjardins, M. Can. J. Chem. 1994, 72, 2312-2317; (e) Prager, R. H.; Schafer, K.; Hamon, D. P. C.; Massy-Westropp, R. A. Tetrahedron 1995, 51, 11465-11472; (f) Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1302-1306; (g) Langlois, N.; Dahuron, N.; Wang, H.-S. Tetrahedron 1996, 52, 15117-15126; (h) Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 1195-1196; (i) Brenna, E.; Carraccia, N.; Fuganti, C.; Fuganti, D.; Graselli, P. Tetrahedron: Asymmetry 1997, 8, 3801-3805.
    • (1996) Tetrahedron , vol.52 , pp. 15117-15126
    • Langlois, N.1    Dahuron, N.2    Wang, H.-S.3
  • 26
    • 0031575602 scopus 로고    scopus 로고
    • (h)
    • For some examples of the asymmetric synthesis of (-)-baclofen and derivatives see: (a) Chênevert, R.; Desjardins, M. Tetrahedron. Lett. 1991, 32, 4249-4250; (b) Herdeis, C.; Hubmann, H. P. Tetrahedron: Asymmetry 1992, 3, 1213-1221; (c) Schoenfelder, A.; Mann, A.; Le Coz, S. Synlett 1993, 63-64; (d) Chênevert, R.; Desjardins, M. Can. J. Chem. 1994, 72, 2312-2317; (e) Prager, R. H.; Schafer, K.; Hamon, D. P. C.; Massy-Westropp, R. A. Tetrahedron 1995, 51, 11465-11472; (f) Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1302-1306; (g) Langlois, N.; Dahuron, N.; Wang, H.-S. Tetrahedron 1996, 52, 15117-15126; (h) Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 1195-1196; (i) Brenna, E.; Carraccia, N.; Fuganti, C.; Fuganti, D.; Graselli, P. Tetrahedron: Asymmetry 1997, 8, 3801-3805.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1195-1196
    • Mazzini, C.1    Lebreton, J.2    Alphand, V.3    Furstoss, R.4
  • 27
    • 0030844225 scopus 로고    scopus 로고
    • (i)
    • For some examples of the asymmetric synthesis of (-)-baclofen and derivatives see: (a) Chênevert, R.; Desjardins, M. Tetrahedron. Lett. 1991, 32, 4249-4250; (b) Herdeis, C.; Hubmann, H. P. Tetrahedron: Asymmetry 1992, 3, 1213-1221; (c) Schoenfelder, A.; Mann, A.; Le Coz, S. Synlett 1993, 63-64; (d) Chênevert, R.; Desjardins, M. Can. J. Chem. 1994, 72, 2312-2317; (e) Prager, R. H.; Schafer, K.; Hamon, D. P. C.; Massy-Westropp, R. A. Tetrahedron 1995, 51, 11465-11472; (f) Yoshifuji, S.; Kaname, M. Chem. Pharm. Bull. 1995, 43, 1302-1306; (g) Langlois, N.; Dahuron, N.; Wang, H.-S. Tetrahedron 1996, 52, 15117-15126; (h) Mazzini, C.; Lebreton, J.; Alphand, V.; Furstoss, R. Tetrahedron Lett. 1997, 38, 1195-1196; (i) Brenna, E.; Carraccia, N.; Fuganti, C.; Fuganti, D.; Graselli, P. Tetrahedron: Asymmetry 1997, 8, 3801-3805.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 3801-3805
    • Brenna, E.1    Carraccia, N.2    Fuganti, C.3    Fuganti, D.4    Graselli, P.5
  • 29
    • 0003828015 scopus 로고
    • (b) Wiley-Intersciences: New York
    • (b) Tidwell, T. T. Ketenes; Wiley-Intersciences: New York, 1995.
    • (1995) Ketenes;
    • Tidwell, T.T.1
  • 31
    • 0011231534 scopus 로고
    • The chiral base was prepared according to a procedure described by
    • The chiral base was prepared according to a procedure described by Eleveld, M. B.; Hogeveen, H.; Schudde, E. P. J. Org. Chem. 1986, 51, 3635-3642; see also, Marshall, J. A.; Lebreton, J. J. Am. Chem. Soc. 1988, 110, 2925-2931.
    • (1986) J. Org. Chem. , vol.51 , pp. 3635-3642
    • Eleveld, M.B.1    Hogeveen, H.2    Schudde, E.P.3
  • 32
    • 0023906601 scopus 로고
    • see also
    • The chiral base was prepared according to a procedure described by Eleveld, M. B.; Hogeveen, H.; Schudde, E. P. J. Org. Chem. 1986, 51, 3635-3642; see also, Marshall, J. A.; Lebreton, J. J. Am. Chem. Soc. 1988, 110, 2925-2931.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 2925-2931
    • Marshall, J.A.1    Lebreton, J.2
  • 33
    • 0344444497 scopus 로고    scopus 로고
    • D -156
    • D -156.
  • 35
    • 0018718521 scopus 로고
    • Borka, L. Acta Pharm. Suec. 1979, 16, 345-348; Chem. Abstr. 1980, 92, 82536r.
    • (1979) Acta Pharm. Suec. , vol.16 , pp. 345-348
    • Borka, L.1
  • 36
    • 0018718521 scopus 로고
    • Borka, L. Acta Pharm. Suec. 1979, 16, 345-348; Chem. Abstr. 1980, 92, 82536r.
    • (1980) Chem. Abstr. , vol.92
  • 39
    • 0000448885 scopus 로고
    • (c) for the preparation of the Zn-Cu couple see:
    • (c) for the preparation of the Zn-Cu couple see: Brady, W. T.; Liddell, H. G.; Vaughan, W. L. J. Org. Chem. 1966, 31, 626-628.
    • (1966) J. Org. Chem. , vol.31 , pp. 626-628
    • Brady, W.T.1    Liddell, H.G.2    Vaughan, W.L.3


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