The synthesis of enantiomerically pure, symmetrically substituted cyclopropane phosphonic acids - a constrained analog of the GABA antagonist phaclophen

Tetrahedron Letters

Volumn 38, Issue 7, 1997, Pages 1103-1106

  Hanessian, Stephen ^a   Cantin, Louis David ^a   Roy, Stéphan ^a   Andreotti, Daniele ^a   Gomtsyan, Arthur ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0031575630     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02518-X     Document Type: Article

References (46)

1. 1. Hilderbrand, R.L. In The Role of Phosphonates in Living Systems; CRC Press: Boca Raton, FL 1983. Neuzil, E.; Cassaigne, A. Exp. Ann. Biochim. Med. 1980, 34, 165.
2. 1. Hilderbrand, R.L. In The Role of Phosphonates in Living Systems; CRC Press: Boca Raton, FL 1983. Neuzil, E.; Cassaigne, A. Exp. Ann. Biochim. Med. 1980, 34, 165.
3. 2. Sikorski, J.A.; Logusch, E.W. In Handbook of Organophosphorus Chemistry, Engel, R. Ed.; Marcel Dekker, Inc.: New York, 1992, p. 739; see also Eto, M., p. 807.
4. 2. Sikorski, J.A.; Logusch, E.W. In Handbook of Organophosphorus Chemistry, Engel, R. Ed.; Marcel Dekker, Inc.: New York, 1992, p. 739; see also Eto, M., p. 807.
5. 3. Flame retardants: Weil, E.D. In Handbook of Organophosphorus Chemistry, Engel, R. Ed.; Marcel Dekker, Inc. New York, 1992, p. 683; metal chelates: Hutchinson, D.W.; Naylor, M,; Semple, G. Chem. Scripta. 1986, 26, 91.
6. 3. Flame retardants: Weil, E.D. In Handbook of Organophosphorus Chemistry, Engel, R. Ed.; Marcel Dekker, Inc. New York, 1992, p. 683; metal chelates: Hutchinson, D.W.; Naylor, M,; Semple, G. Chem. Scripta. 1986, 26, 91.
7. 4. Sikorski, J.A.; Miller, M.J,; Braccolino, D.S.; Cleary, D.G.; Corey, S.D.; Font, J.L.; Gruys, K.J.; Han, C.Y.; Lin, K.-C.; Pansegrau, P.D.; Ream, J.E.; Schnur, D.; Shah, A.; Walker, M.C. Phosphorus, Sulfur, and Silicon 1993, 76, 115.
8. 5. Diana, G.D.; Pevear, D.; Young, D.C. Ann. Rep. Med. Chem. 1989, 24, 129. Pauwels, R.; Balzarini, J.; Schols, D.; Baba, M.; Desmyter, J.; Rosenberg, I.; Holy, A.; De Clercq, E. Antimicrob. Agents and Chemother. 1988, 32, 1025.
9. 5. Diana, G.D.; Pevear, D.; Young, D.C. Ann. Rep. Med. Chem. 1989, 24, 129. Pauwels, R.; Balzarini, J.; Schols, D.; Baba, M.; Desmyter, J.; Rosenberg, I.; Holy, A.; De Clercq, E. Antimicrob. Agents and Chemother. 1988, 32, 1025.
10. 6. Cameron, D.G.; Hudson, H.R.; Pianka, M, Phosphorus, Sulfur, and Silicon 1993, 83, 21.
11. 7. Hendlin, D.; Stapley, E.O.; Jackson, M.; Wallick, H.; Miller, A.K.; Wolf, F.J.; Miller, T.W.; Chaiet, L.; Kahan, G.M.; Foltz, EL.; Woodruff, H.B.; Mata, J.M.; Hernandez, S.; Mochales, S. Science 1969, 166, 122.
12. 8. Malachowski, W.P.; Coward, J.K. J. Org. Chem. 1994, 59, 7625.
13. 9. Engel, R. Chem. Rev. 1977, 77, 349.
14. 10. Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. Bongini, A.; Camerini, R.; Panunzio, M. Tetrahedron. Asym. 1996, 7, 1467. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995. 60, 6656. Drescher, M.; Li, Y.-F; Hammerschmidt, F. Tetrahedron 1995, 51, 4933. Dhawan, B.; Redmore, D. Phosphorus and Sulphur 1987, 32, 119. See also ref. 14.
15. 10. Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. Bongini, A.; Camerini, R.; Panunzio, M. Tetrahedron. Asym. 1996, 7, 1467. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995. 60, 6656. Drescher, M.; Li, Y.-F; Hammerschmidt, F. Tetrahedron 1995, 51, 4933. Dhawan, B.; Redmore, D. Phosphorus and Sulphur 1987, 32, 119. See also ref. 14.
16. 10. Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. Bongini, A.; Camerini, R.; Panunzio, M. Tetrahedron. Asym. 1996, 7, 1467. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995. 60, 6656. Drescher, M.; Li, Y.-F; Hammerschmidt, F. Tetrahedron 1995, 51, 4933. Dhawan, B.; Redmore, D. Phosphorus and Sulphur 1987, 32, 119. See also ref. 14.
17. 10. Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. Bongini, A.; Camerini, R.; Panunzio, M. Tetrahedron. Asym. 1996, 7, 1467. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995. 60, 6656. Drescher, M.; Li, Y.-F; Hammerschmidt, F. Tetrahedron 1995, 51, 4933. Dhawan, B.; Redmore, D. Phosphorus and Sulphur 1987, 32, 119. See also ref. 14.
18. 10. Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. Bongini, A.; Camerini, R.; Panunzio, M. Tetrahedron. Asym. 1996, 7, 1467. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995. 60, 6656. Drescher, M.; Li, Y.-F; Hammerschmidt, F. Tetrahedron 1995, 51, 4933. Dhawan, B.; Redmore, D. Phosphorus and Sulphur 1987, 32, 119. See also ref. 14.
19. 11. Horiguchi, M.; Kandatsu, M. Nature 1959, 184, 901.
20. 12. Studer, A.; Seebach, D. Heterocycles 1995, 40, 357. Isbell, A.F.; Berry, J.P.; Tansey, L.W. J. Org. Chem. 1972, 37, 4399. Barycki, J.; Mastalerz, P.; Soroka, M. Tetrahedron Lett. 1970, 3147.
21. 12. Studer, A.; Seebach, D. Heterocycles 1995, 40, 357. Isbell, A.F.; Berry, J.P.; Tansey, L.W. J. Org. Chem. 1972, 37, 4399. Barycki, J.; Mastalerz, P.; Soroka, M. Tetrahedron Lett. 1970, 3147.
22. 12. Studer, A.; Seebach, D. Heterocycles 1995, 40, 357. Isbell, A.F.; Berry, J.P.; Tansey, L.W. J. Org. Chem. 1972, 37, 4399. Barycki, J.; Mastalerz, P.; Soroka, M. Tetrahedron Lett. 1970, 3147.
23. 13. Edmundson, R.S. Dictionary of Organophosphorus Compounds; Chapman and Hall Ltd: London, 1988.
24. 14. a. Mikolajczyk, M.; Lyzwa, P.; Drabowicz, J.; Wieczorek, M.W.; Blaszczyk, J. Chem. Commun. 1996, 1503.
25. b. Smith, A.B., III; Yager, K.M.; Taylor, C.M. J. Am. Chem. Soc. 1995, 117, 10879.
26. c. Hanessian, S.; Bennani, Y.L. Tetrahedron Lett. 1990, 31, 6465.
27. d. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D.E. Tetrahedron Lett. 1990, 31, 5587.
28. e. Minowa, N.; Hirayama, M.; Fukatsu, S. Tetrahedron Lett. 1984, 25, 1147.
29. 15. Morphy, J.R.; Beeley, N.R.A; Boyce, B.A.; Leonard, J.; Mason, B., Millican, A.; Millar, K.; O'Connell. J.P.; Porter, J. Bioorg. & Med. Chem. Lett. 1994, 4, 2747. Grobelny, D.; Goli, U.B.; Galardy, R.E. Biochem. J. 1985, 232, 15.
30. 15. Morphy, J.R.; Beeley, N.R.A; Boyce, B.A.; Leonard, J.; Mason, B., Millican, A.; Millar, K.; O'Connell. J.P.; Porter, J. Bioorg. & Med. Chem. Lett. 1994, 4, 2747. Grobelny, D.; Goli, U.B.; Galardy, R.E. Biochem. J. 1985, 232, 15.
31. 16. Groth, U.; Lehmann, L.; Richter, L.; Schöllkopf, U. Lieb. Ann. Chem. 1993, 427. Erion, M.D.; Walsh, C.T. Biochemistry 1987, 26, 3417. Diel, P.J.; Maier, L. Phosphorus and Sulfur 1984, 20, 313
32. 16. Groth, U.; Lehmann, L.; Richter, L.; Schöllkopf, U. Lieb. Ann. Chem. 1993, 427. Erion, M.D.; Walsh, C.T. Biochemistry 1987, 26, 3417. Diel, P.J.; Maier, L. Phosphorus and Sulfur 1984, 20, 313
33. 16. Groth, U.; Lehmann, L.; Richter, L.; Schöllkopf, U. Lieb. Ann. Chem. 1993, 427. Erion, M.D.; Walsh, C.T. Biochemistry 1987, 26, 3417. Diel, P.J.; Maier, L. Phosphorus and Sulfur 1984, 20, 313
34. 17. a. Hanessian, S.; Bennani, Y.L.; Hervé, Y. Synlett. 1993, 35.
35. b. Hanessian, S.; Bennani, Y.L.; Delorme, D. Tetrahedron Lett. 1990, 31, 6461.
36. 18. Hanessian, S.; Gomtsyan, A.; Payne, A.; Hervé, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032.
37. 19. Nomura, M.; Kanemasa, S. Tetrahedron Lett. 1994, 35, 143. Bernardi, A.; Capelli, A.M.; Comotti, A.; Gennari, C.; Scolastico, C. Tetrahedron Lett. 1991, 32, 823.
38. 19. Nomura, M.; Kanemasa, S. Tetrahedron Lett. 1994, 35, 143. Bernardi, A.; Capelli, A.M.; Comotti, A.; Gennari, C.; Scolastico, C. Tetrahedron Lett. 1991, 32, 823.
39. 20. Kranz, M.; Denmark, S.E. J. Org. Chem. 1995, 60, 5867, and references cited therein.
40. 21. Morizawa, Y.; Yasuda, A.; Uchida, K. Tetrahedron Lett. 1986, 27, 1833. Gschwend, H.W.; Rodriguez, H.R. Org. React. 1979, 26, 1.
41. 21. Morizawa, Y.; Yasuda, A.; Uchida, K. Tetrahedron Lett. 1986, 27, 1833. Gschwend, H.W.; Rodriguez, H.R. Org. React. 1979, 26, 1.
42. 22. Kerr, D.I.B.; Ong, J.; Prager, R.H.; Gynther, B.D.; Curtis, D.R. Brain Res. 1987, 405, 150.
43. 23. Charette, A.B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721.
44. 24. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30. 2151.
45. 25. Froestl, W.; Mickel, S.J.; Hall. R.G.; von Sprecher, G.; Strub, D.; Baumann, P.A.; Brugger, F.; Gentsch, C.; Jaekel, J.; Olpe, H.-R.; Rihs, G.; Vassout, A.; Waldmeier, P.C.; Bittiger, H. J. Med. Chem. 1995, 38, 3297.
46. 26. Knöpfel, T.; Kuhn, R.; Allgeier, H. J. Med Chem. 1995, 38, 1417.