(-)-15-Deoxyspergualin: A new and efficient enantioselective synthesis which allows the definitive assignment of the absolute configuration

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9723-9727

  Durand, Philippe ^a,b   Richard, Philippe ^a   Renaut, Patrice ^a  

^a Laboratoires Fournier SA   (France)

^b UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

15 DEOXYSPERGUALIN; SPERGUALIN DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; IMMUNOSUPPRESSIVE TREATMENT; KIDNEY GRAFT REJECTION;

EID: 0032567482     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9811118     Document Type: Article

References (61)

1. Takeuchi, T.; Iinuma, H.; Kunimoto, S.; Masada, T.; Ishizuka, M.; Takeuchi, M.; Hamada, M.; Naganawa, H.; Kondo, S.; Umezawa, H. J. Antibiot. 1981, 34, 1619-1621.
2. Umezawa, H.; Kondo, S.; linuma, H.; Kunimoto, S.; Ikeda, Y.; Iwazawa, H.; Ikeda, D.; Takeuchi, T. J. Antibiot. 1981, 34, 1622-1624.
3. Kondo, S.; Iwasawa, H.; Ikeda, D.; Umeda, Y.; Ikeda, Y.; linuma, H.; Umezawa, H. J. Antibiot. 1981, 34, 1625-1627.
4. Iwasawa, H.; Kondo, S.; Ikeda, D.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1982, 35, 1665-1669.
5. An eutomer is the more potent of a pair of biologically active enantiomers as defined in: Pedro, A.; Lehmann, F. Trends in Pharm. Sci. 1986, 281.
6. Umeda, Y.; Moriguchi, M.; Kuroda, H.; Nakamura, T.; linuma, H.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1985, 38, 886-98.
7. (b) Bergeron, R. J-; McManis, J. S. J. Org. Chem. 1987, 52, 1700-03.
8. Umeda, Y.; Moriguchi, M-; Ikai, K.; Kuroda, H.; Nakaruma, T.; Fujii, A.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1987, 40, 1316-1324.
9. Maeda, K.; Umeda, Y.; Saino, T. Ann. N.Y. Acad. Sci. 1993, 685, 123-135 and references therein.
10. One example of chemical asymmetric synthesis of α-hydroxyglycine compound by asymmetric reduction of oxalic derivatives with low stereoinduction: O'Donnell, M. J.; Chen, N.; Zhou, C.; Murray, M.; Kubiak, C. P.; Yang, F.; Stanley, G. C. J. Org. Chem. 1997, 62, 3962-75.
11. Chen, S.-T.; Hsiao, S.-C.; Chiori, A.-J.; Wu, S.-H.; Wang, K.-T. J. of Chinese Chemical Society 1992, 39, 91-99.
12. (b) Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1992, 57, 6769-78.
13. Kawai, M.; Hosoda, K.; Omori, Y.; Yamada, K.; Yamamura, H.; Butsugan, Y. Peptide Chemitry 1994: M. Ohno (Ed) 32nd Symposium, Oct 1994 Fukuoka, 161-4.
14. Bogenstätter, M.; Steglich, W. Tetrahedron 1997, 53, 7267-74.
15. (e) Patel, R. N.; Banerjee, A.; Szarka, L. J. Tetrahedron: Asymmetry, 1997, 8, 1767-1771.
16. Young, S. D.; Tamburine, P. P. J. Am. Chem. Soc. 1989, 111, 1933-4.
17. (b) Fing, D.; Mounier, C. E.; May, S. W. J. Biol. Chem. 1995, 270, 29250-5.
18. Fing, D.; Katopodis, A. G.; May, S. W. J. Am. Chem. Soc. 1992, 114, 3998-4000.
19. Shiono, S.; Harada, K. Bull. Chem. Soc. Jpn 1985, 58, 1061-2.
20. (e) Brown, A. R.; Ramage, R. Tetrahedron Lett. 1994, 35, 789-92.
21. (f) Gilvarg, C.; Kingsbury, W. D. U.S. Patent 4, 454, 065, Jun. 12, 1984.
22. (g) Kawahara, T.; Susuki, K.; Iwasaki, Y.; Shimoi, H.; Akita, M.; Moro-oka, Y.; Nishikawa, Y. J. Chem. Soc. Chem. Commun., 1992, 625-6.
23. Kawai, M.; Omori, Y.; Yamamura, H.; Butsugan, Y. Tetrahedron: Asymmetry 1992, 3, 1019-20.
24. a) We have recently patented the synthesis of (-) DSG and analogues using this approach: Lebreton, L.; Renaut, P.; Durand, P. PCT Int. Appl. WO 9624579, Aug. 15, 1996.
25. (b) During preparation of the manuscript of this publication, a patent from BMS company has described a similar approach. Wang, X.; Thottahil, J. K Ear. Pat. Appl. EP 765, 866, Apr. 2, 1997.
26. Kawai, M.; Neogi, P.; Khattri, P. S.; Butsugan, Y. Chemistry Letter 1990, 577-80.
27. Putnam, D.; Kopecek, J. J. Bioconjugate Chem. 1995, 6, 483-92.
28. Kawai, M.; Hosoda, K.; Omori, Y.; Yamada, K.; Yamamura, S.; Yamamura, H.; Butsugan, Y. Synth. Commun. 1996, 26, 1545-54.
29. (b) Zoller, U.; Ben-Ishai, D. Tetrahedron, 1975, 31, 863-866.
30. O'Donnell, M. J.; Bennett, W. D.; Polt, R. L. Tetrahedron Lett. 1985, 26, 695-8.
31. (b) Apitz, G.; Jäger, M.; Jaroch, S.; Krayzel, M.; Schäffeler, L.; Steglich, W. Tetrahedron 1993, 49, 8223-32.
32. Easton, C. J.; Pitt, M. J. Tetrahedron Lett. 1990, 31, 3471-4.
33. (b) Easton, C. J.; Tan, E. W.; Hay, M. P. J. Chem. Soc. Chem. Commun. 1989, 385-7.
34. Syntheses of α-halogenoglycines from α-thioalkylglycines: see ref 16bl
35. Syntheses of α-halogenoglycines from α-alkoxyglycines: Kohn, H.; Sawhney, K N.; Le Gall, P.; Roberton, D. W.; Leander, J. D. J. Med. Chem. 1991, 34, 2444-52.
36. Syntheses of α-halogenoglycines from glycines: (a) Kober, R.; Steglich, W. Liebigs Ann. Chem. 1983, 4, 599-609.
37. (b) Williams, R. M.; Sinclair, P. J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547-57.
38. see ref 16b
39. Hamon, D. P. G.; Razzino, P.; MassyWestropp, R. A. J. Chem. Soc. Chem. Commun. 1991, 332-3.
40. Syntheses of α-halogenoglycines from α-hydroxyglycines: a) Bernstein, Z.; Ben-Ishai, D. Tetrahedron 1977, 33, 881-3.
41. (b) Bateson, J. H.; Baxter, A. J. G.; Roberts, P. M.; Smale, T. C.; Southgate, R. J. Chem. Soc., Perkin Trans. 1 1981, 3242-9.
42. Chiono, S.; Harada, K. Bull. Chem. Soc. Jpn. 1985, 58, 1061-2.
43. Alks, V.; Sufrin, J. R. Synth. Commun. 1989, 19, 1479-86.
44. (e) Daumas, M.; Vo Quang, L.; Le Goffic, F. Synth. Commun. 1990, 20, 3395-3401.
45. (0 Ebeling, S. C. J. Prakt. Chem. 1994, 336, 330-332.
46. 4 hydrolysis of the nitrile compound afforded a mixture of 4 (32%) and the symmetrical bis(7-bromoheptane)imide(24%).
47. For recent improvement of the procedure and references for the synthesis of alkyl azide see: Alvarez, S. G.; Alvarez M. T. Synthesis, 1997, 4, 413-414.
48. Optically active benzylic alcohols, S-(-)-1-phenyl ethanol, S-(-)-phenyl-1-butanol,S-(-)-1-(1-naphthyl)ethanol, S-(-)-α-methyl-2-naphthalenemethanol, S-(+)-1-indanol, R-(-)-α-tetralol are commercially available. A slight induction (d.e. 30%) was observed with the latter two compounds as determined by NMR analysis.
49. Nishizawa, R.; Takei, Y.; Yoshida, M.; Tomiyoshi, T.; Saino, T.; Nishikawa, K.; Nemoto, K.; Takahashi, K.; Fujii, A.; Nakamura, T.; Takita, T.; Takeuchi, T. J. Antibiotic 1988, 41, 1629-43.
50. Gilchrist, T. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 8; pp 381399.
51. Knouzi, N.; Vaultier, M.; Carrie, R. Bull. Soc. Chim. Fr. 1985, 5, 815-9.
52. Tian, Z.; Edward, P.; Roeske, R. W. Int. J. Pept. Protein Res. 1992, 40, 119-26.
53. Auerbach, J.; Zamore, Me. F.; Weinreb, S. M.J. Org. Chem. 1976, 41, 725-26.
54. Mayo, D. J.; Tomasella, F. P.; Noroski, J. E. J. Pharm. Biochem. Analysis 1996, 14, 457-463.
55. The author has deposited crystallographic data for 7b with the Cambridge Crystallographic Data Center. The data can be obtained, on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, U.K.
56. We have checked that there was no epimerisation during saponification of 7a by reesterification of the crude product with an ethereal diazomethane solution and analysis of the crude product by NMR. Attempts to purify and better characterize the acid intermediate revealed its instability.
57. See ref 8.
58. (b) See ref 13a.
59. Renaut, P.; Lebreton, L.; Dutartre, P.; Derrepas, P.; Samreth, S. Eur. Pat. Appl. EP 600762, Jun 8, 1994.
60. Lebreton, L.; Renaut, P.; Dumas C. Eur. Pat. Appl. EP 743300, Nov. 20, 1996.
61. Kawahara, T.; Susuki, K.; Iwasaki, Y.; Shimoi, H.; Akita, M.; Moro-oka, Y.; Nishikawa, Y. J. Chem. Soc., Chem. Commun. 1992, 625-626.