First synthesis of (±)-10β-hydroxy-13β methylcyclohexa[a]quinolizidine. A convenient route to the ABC-part of 8- azasteroids

Tetrahedron

Volumn 55, Issue 30, 1999, Pages 9269-9282

  Célanire, Sylvain ^a   Salliot Maire, Isabelle ^a   Ribéreau, Pierre ^a   Godard, Alain ^a   Quéguiner, Guy ^a  

^a IRCOF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

10BETA HYDROXY 13BETA METHYLCYCLOHEXA[A]QUINOLIZIDINE; 8 AZASTEROID; QUINOLIZIDINE DERIVATIVE; STEROID; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG CONFORMATION; DRUG SYNTHESIS; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY; STEROIDOGENESIS; STRUCTURE ACTIVITY RELATION;

EID: 0033598002     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00497-4     Document Type: Article

References (62)

1. Current adress: Laboratoire de Chimie Organique Fine et Hétérocyclique, INSA de Rouen; IRCOF.
2. Current adress: Centre Régional Universitaire de Spectroscopie, IRCOF, Université de Rouen.
3. For general reviews on structure-activity relationships of azasteroids in the treatment of Benign Prostatic Hyperplasia, see: (a) Kenny, B.; Ballard, S.; Blagg, J.; Fox, D. J. Med. Chem. 1997, 40, 1293-1315.
4. (b) Li, X.; Chen, C.; Singh, S.M.; Labrie, F. Steroids 1995, 60, 430-441 and references cited therein.
5. Examples of syntheses and biological evaluations of: -azasteroids: (a) Rasmusson, G.H.; Reynolds, G.F.; Steinberg, N.G.; Walton, E.; Patel, G.F.; Liang, T.; Cascieri, M.A.: Cheung, A.H.; Brooks, J.R.; Berman, C. J. Med. Chem. 1986, 29, 2298-2315.
6. (b) Rasmusson, G.H.; Reynolds, G.F.; Utne, T.; Jobson, R.B.; Primka, R.L.; Berman, C.; Brooks, J.R. J. Med Chem. 1984, 23, 1690-1701. 6-azasteroids
7. (c) Frye, S.V.; Haffner, C.D.; Maloney, P.R.; Hiner, R.N.; Dorsey, G.F.; Noe, R.A.; Unwalla, R.J.; Batchelor, K.W.; Bramson, H.N.; Stuart, J.D.; Schweiker, S.L; van Arnold, J.; Bickett, D.M.; Moss, M.L.; Tian, G.; Lee, F.W.; Tippin, T.K.; James, M.K. J. Med. Chem. 1995, 38, 2621-2627.
8. (d) Frye, S.V.; Haffner, C.D.; Maloney, P.R.; Mook, Jr., R.A.; Dorsey, G.F.; Hiner, R.N.; Cribbs, C.M.; Wheeler, T.N.; Ray, J.A.; Andrews, R.C.; Batchelor, K.W.; Bramson, H.N.; Stuart, J.D.; Schweiker, S.L; van Arnold, J. J. Med. Chem. 1994, 37, 2352-2360. 3-azasteroids:
9. (e) Haffner, C. Tetrahedron Lett. 1994, 35, 1349-1352.
10. Counsell, R.E.; Klimstra, P.D.; Nysted, L.N.; Ranney, R.E. J. Med. Chem. 1965, 8, 45-48.
11. (a) Sutherland, A.J.; Sutherland, J.K.; Crowley, P.J. J. Chem. Soc., Perkin Trans. I 1997, 349-354.
12. (b) Dolle, R.E.; Allaudeen, H.S.; Kruse, L.I. J. Med. Chem. 1990, 33, 877-880.
13. (c) Barton, D.H.R.; Lusinchi, X.; Menéndez, A.M.; Milliet, P. Tetrahedron 1983, 39, 2201-2205.
14. 5-setroid isomerase: (a) Brandt, M.; Levy, M.A. Biochemistry 1989, 28, 140-148. Neuromuscular bloking agents:
15. (b) Abraham, J.; Jindal, D.P.; Singh, H. Indian J. Chem., Sect. B 1992, 31, 566-569. Antimicrobial agents:
16. (c) Chesnut, R.W.; Durham, N.N.; Brown, R.A., Mandsley, E.A.; Berlin, K.D. Steroids 1976, 27, 525.
17. (d) Solomons, W.E.; Doorenbos, N.J. J. Pharm. Sci. 1974, 63, 19-22.
18. (a) Lamour, P. Synthesis of Substituted Piperidines with Potential Biological Activity University of Rouen, 1993.
19. (b) Mabire, D. Syntheses and Applications of Azadecalines, Tetrahydroisoquinolines and Polyfunctional Derivatives University of Rouen, 1990.
20. Rahier, A.; Taton, M.; Schmitt, P.; Benveniste, P.; Place, P.; Anding, C. Phytochemistry 1985, 24, 1223-1232.
21. Godard, A.; Lamour, P.; Ribereau, P.; Quéguiner, G. Tetrahedron 1995, 51, 3247-3264.
22. (a) Barth, M.M.; Binet, J.L.; Thomas, D.M.; deFornel, D.C.; Samreth, S.; Schuber, F.J.; Renaut, P.P. J. Med. Chem. 1996, 39, 2302-2312 and references cited therein.
23. (b) Wannamaker, M. W.; Waid, P.P.; Van Sickle, W.A.; McCarthy, J.R.; Wilson, P.K.; Schatzman, G.L.; Moore, W.R. J. Med. Chem. 1992, 35, 3581-3583.
24. Marquart, A.L.; Schatzman, G.L.; Peet, N.P.; Moore, W.R.; Huber, E.W.; Gallion, S.L.; Angelastro, M.R. Bioorganic & Medicinal Chemistry Letters 1994, 4, 1317-1318.
25. (a) Stach, D.; Zheng, Y.F.; Perez, A.L.; Oehlschlager, A.C.; Abe, I.; Prestwich, G.D.; Hartman, P.G. J. Med. Chem., 1997, 40, 201-209.
26. (b) Abe, I.; Rohmer, M.; Prestwich, G.D. Chem. Rev. 1993, 93, 2189-2206.
27. (a) Huisman, H.O. In Steroids. John, W.F., Ed.; International Review of Science, Organic Chemistry Series 1, Buttreworths: London, 1973, Vol. 8, Chap. 9, pp.235-267;
28. (b) Huisman, H.O. Angew. Chem Int. Ed. 1971, 10, 450-459.
29. (c) Huisman, H.O. Bull. Soc. Chim. Fr. 1968, 1, 13-24.
30. (a) Brown, R.E.; Lustgarten, D.M.; Stanaback, R.J.; Meltzer, R.I. J. Org. Chem. 1966, 31, 1489-1495.
31. (b) Meyers, A.I.; Munoz, G.G.; Sobotka, W.; Baburao, K. Tetrahedron Lett. 1965, 4, 255-260.
32. Meyers, A.I.; Elworthy, T.R. J. Org. Chem. 1992, 57, 4732-4740.
33. (a) Back, T.G.; Chau, J.H.-L.; Codding, P.W.; Gladstone, P.L.; Jones, D.H.; Morzycki, J.W.; Roszak, A.W. J. Org. Chem., 1992, 57, 4110-4121.
34. (b) Rodewald, W.J.; Achmatowicz, B. Tetrahedron 1971, 27, 5467-5473.
35. Guarna, A.; Belle, C.; Machetti, F; Occhiato, E.G.; Cassiani C.; Comerci, A.; Danza, G.; De Bellis, A.; Dini, S.; Marrucci, A.; Serio, M. J. Med. Chem. 1997, 40, 1112-1129 and references cited therein.
36. Quéguiner, G.; Marsais, F.; Snieckus, V.; Epsztajn, J. Advances in Heterocyclic Chemistry, ed. A.R. Katritzky, Academic Press, San Diego, 1991, Vol. 52, pp.187-304.
37. (a) Pasquinet, E.; Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron 1998, 54, 8771-8782.
38. (b) Pasquinet, E.; Rocca, P.; Godard, A.; Marsais, F.; Quéguiner, G. J. Chem. Soc., Perkin Trans. I 1998, 3807-3812.
39. (a) Katritzky, A.R.; Rees, C.W. Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford, 1984, 2, p.333;
40. (b) Crabb, T.A.; Fallah, A. J. Chem. Soc., Perkin Trans. 2 1992, 1335-1342.
41. (c) Mathis, C.; Hogen-Esch, T.E. J. Am. Chem. Soc. 1982, 104, 634-635.
42. (a) Cassity, R.P.; Taylor, L.T.; Wolfe, J.F. J. Org. Chem. 1978, 43, 2256-2258;
43. (b) Beumel Jr, O.F.; Smith, W.N.; Rybalka, B. Synthesis 1974, 43-45.
44. The preparation of the N-(2,2-dimethoxyacetyl)piperidine as electrophile was realised on a multi-scale synthesis in two steps from glyoxylic acid: tandem esterification-acetalization reaction provide methyldimethoxyacetal, which was allowed to react with piperidine to give the desired product in a % overall yield. See also: Cameron, A.G.; Hewson, A.T. J. Chem. Soc., Perkin Trans. 1 1983, 2979-2982. (matrix presented)
45. Greenhill, J.V.; Loghmani-Khouzani, H.; Maitland, D.J. Tetrahedron 1988, 44, 3319-3326.
46. For reviews, see: (a) Gawley, R.E. Synthesis 1976, 777-794.
47. (b) Jung, M.E. Tetrahedron 1976, 32, 3-31.
48. Delamare, M.; Rameix, N.; Célanire, S. and Ribereau, P.; unpublished results.
49. Earnshaw, C.; Wallis, C.J.; Warren, S. J. Chem. Soc., Perkin Trans. I 1979, 3099-3106.
50. Keinan, E.; Greenspoon, N. Comprehensive Organic Synthesis; Pergamon Press, Oxford, 1991, 8, p523.
51. Pearlman, W.M. Tetrahedron Lett. 1967, 17, 1663-1664.
52. We are grateful to Mr. Gérard Goussot, Laboratory of Preparative Chromatography, Janssen-Cilag (Val-de-Reuil, France) for its fruitfull help towards their purification.
53. Gung, B.W. Tetrahedron, 1996, 52, 5263-5301.
54. Czernecki, S.; Georgoulis, C.; Provelenghiou, C. Tetrahedron Lett. 1976, 39, 3535-3536.
55. For examples of quaternarizations of pyridine nucleus in the synthesis of alkaloids, see: (a) Dobbs, A.P.; Jones, K.; Veal, K.T. Tetrahedron Lett. 1997, 38, 5383-5386.
56. (b) Ciufolini, M.A.; Roschangar, F. J. Org. Chem. 1996, 118, 12082-12089.
57. (c) Boekeilheide, V.; Fritz, H.; Ross, J.M.; Kaempfen, H.X. Tetrahedron 1964, 20, 33-41.
58. Sajiki, H.; Hirota, K. Tetrahedron 1998, 54, 13981-13996.
59. For general reviews on spectroscopic methods in the analysis of quinolizidine derivatives, see: (a) Crabb, T.A.; Katritzky, A.R. Adv. Het. Chem. 1984, 36, 1-175 and references cited therein.
60. (b) Crabb, T.A.; Newton, R.F.; Jackson, D. Chem. Rev. 1971, 71, 109-128.
61. Bohlmann, F. Chem. Ber. 1958, 91, 2157-2167.
62. Analogous hydroxyquinolizidines were early reported towards the steric structure of Securinine; Saito, S.; Kotera, K.; Shimagematsu, N; Ide, A; Sugimoto, N.; Horii, Z.; Hanakoa, M.; Yamawaki, Y.; Tamura, Y. Tetrahedron 1963, 19, 2085-2099.