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DOI: 10.1039/A804660C (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 2629-2634

First asymmetric synthesis of the Kelatorphan-like enkephalinase inhibitor (1S,2R,2′S[hair space])-2-[2′-(N-hydroxycarbamoylmethyl)-3′-phenylpropionylamino]cyclohexane-1-carboxylic acid

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Stephen G. Davies and Darren J. Dixon

Abstract

The first asymmetric synthesis of Kelatorphan-like enkephalinase inhibitor (1S,2R,2′S[hair space])-2-[2′-(N-hydroxycarbamoylmethyl)-3′-phenylpropionylamino]cyclohexane-1-carboxylic acid is achieved using lithium amide (R)-5 and pyrrolidinone auxiliary (R)-6; the pyrrolidinone auxiliary is used to create (2S[hair space])-benzylsuccinic acid derivative (S[hair space])-4 while lithium amide (R)-5 is used to synthesize tert-butyl (1S,2R)-2-aminocyclohexanecarboxylate 3.

References

  1. (a) T. T. Chau-Pham, Drug Metab. Rev., 1978, 7, 255 CAS; (b) S. H. Snyder, Sci. Am., 1978, 44, 236 Search PubMed; (c) S. H. Snyder, Chem. Eng. News, 1977, 26, 55; (d) E. J. Simon and J. M. Hiller, Ann. Rev. Pharmacol. Toxicol., 1978, 18, 371 CrossRef CAS.
  2. M.-C. Fournie-Zaluski, A. Coulard, R. Bouboutou, P. Chaillet, J. Devin, G. Waksman, J. Costentin and B. P. Roques, J. Med. Chem., 1985, 28, 1158 CrossRef CAS.
  3. J. Xie, J. M. Soleilhac, N. Renwart, J. Peyroux, B. P. Roques and M.-C. Fournie-Zaluski, Int. J. Peptide Protein Res., 1989, 34, 246 Search PubMed.
  4. S. G. Davies, O. Ichihara, I. Lenoir and I. A. S. Walters, J. Chem. Soc., Perkin Trans. 1, 1994, 1411 RSC.
  5. D. J. Dixon and S. G. Davies, Chem. Commun., 1996, 1797 RSC.
  6. D. A. Evans, M. D. Ennis and D. J. Mathre, J. Am. Chem. Soc., 1982, 104, 1737 CrossRef CAS.
  7. S. G. Davies, G. J.-M. Doisneau, J. C. Prodger and H. Sanganee, Tetrahedron Lett., 1994, 35, 2373 CrossRef CAS.
  8. J. J. Plattner, P. A. Marcotte, H. D. Kleinert, H. H. Stein, J. Greer, G. Bolis, A. K. L. Fung, B. A. Bopp, J. R. Luly, H. L. Sham, D. J. Kempf, S. H. Rosenberg, J. F. Dellaria, B. De, I. Merits and T. J. Perun, J. Med. Chem., 1988, 31, 2277 CrossRef CAS.
  9. T. Kurihara, M. Sugizaki, I. Kime, M. Wada and O. Mitsunobu, Bull. Chem. Soc. Jpn., 1981, 54, 2107 CAS.
  10. N. H. Anderson, J. P. Devlin, S. Jones, W. D. Ollis and J. E. Thorpe, J. Chem. Soc., Perkin Trans. 1, 1975, 852 RSC.
  11. (a) J. Pless and W. Bauer, Angew. Chem., Int. Ed. Engl., 1973, 12, 147 Search PubMed; (b) E. N. Chauvel, C. Llorens-Cortès, P. Coric, S. Wilk, B. P. Roques and M.-C. Fournié-Zaluski, J. Med. Chem., 1994, 37, 2950 CrossRef CAS.
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