Diastereoselective synthesis of (–)-N-acetylneuraminic acid (Neu5Ac) from a non-carbohydrate source[hair space]

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Martin Banwell, Chris De Savi and Keith Watson


Abstract

cis-1,2-Dihydrocatechol 2, a product of microbial oxidation of chlorobenzene, has been converted into a protected form, 17, of (–)-Neu5Ac (1) via a fifteen step reaction sequence.


References

  1. M. von Itzstein and R. J. Thompson, Top. Curr. Chem., 1997, 186, 119 CAS and references cited therein.
  2. For the most recently reported chemical synthesis of (–)-Neu5Ac, see T. Takahashi, H. Tsukamoto, M. Kurosaki and H. Yamada, Synlett, 1997, 1065 Search PubMed For a useful review of earlier synthetic studies, see M. P. DeNinno, Synthesis, 1991, 583 CAS.
  3. (a) C.-H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Tetrahedron Organic Chemistry Series Volume 12, Pergamon, Oxford, 1994 and references cited therein Search PubMed; (b) T. Sugai, A. Kuboki, S. Hiramatsu, H. Okazaki and H. Ohta, Bull. Chem. Soc. Jpn., 1995, 68, 3581 CAS and references cited therein.
  4. F. Baumberger and A. Vasella, Helv. Chim. Acta, 1986, 69, 1205 CrossRef CAS.
  5. T.-H. Chan and M.-C. Lee, J. Org. Chem., 1995, 60, 4228 CrossRef CAS.
  6. D. M. Gordon and G. M. Whitesides, J. Org. Chem., 1993, 58, 7937 CrossRef CAS.
  7. For reviews on the applications of cis-1,2-dihydrocatechols in synthesis, see (a) T. Hudlicky, D. A. Entwistle, K. K. Pitzer and A. J. Thorpe, Chem. Rev., 1996, 96, 1195 CrossRef CAS; (b) T. Hudlicky and A. J. Thorpe, Chem. Commun., 1996, 1993 RSC; (c) T. Hudlicky and J. W. Reed, in Advances in Asymmetric Synthesis, ed. A. Hassner, JAI, Greenwich, CT 1995, vol. 1, p. 271 Search PubMed; (d) S. M. Brown and T. Hudlicky, in Organic Synthesis: Theory and Applications, ed. T. Hudlicky, JAI, Greenwich, CT 1993, vol 2, 113 Search PubMed; (e) H. A. J. Carless, Tetrahedron: Asymmetry, 1992, 3, 795 CrossRef CAS; (f) D. A. Widdowson, D. W. Ribbons and S. D. Thomas, Janssen Chim. Acta, 1990, 3 Search PubMed.
  8. S. J. Danishefsky, M. P. DeNinno and S. Chen, J. Am. Chem. Soc., 1988, 110, 3929 CrossRef CAS.
  9. M. Banwell, C. De Savi and K. Watson, Chem. Commun., 1998, 1189 RSC.
  10. T. Hudlicky, T. Nugent and W. Griffith, J. Org. Chem., 1994, 59, 7944 CrossRef CAS.
  11. T. C. Nugent and T. Hudlicky, J. Org. Chem., 1998, 63, 510 CrossRef CAS.
  12. For examples of related reactions, see (a) S. Hanessian, H. Park and R.-Y. Yang, Synlett, 1997, 351 and 353 CAS; (b) M. Banwell, C. De Savi, D. Hockless and K. Watson, Chem. Commun., 1998, 645 RSC.
  13. K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 1992, 57, 2768 CrossRef CAS.
  14. (a) B. ElAmin, G. M. Anantharamaiah, G. P. Royer and G. E. Means, J. Org. Chem., 1979, 44, 3442 CrossRef CAS; (b) B. D. Gray and P. W. Jeffs, J. Chem. Soc., Chem. Commun., 1987, 1329 RSC; (c) A. M. Diederich and D. M. Ryckman, Tetrahedron Lett., 1993, 34, 6169 CrossRef.
  15. A. Marra and P. Sinaÿ, Carbohydr. Res., 1989, 190, 317 CrossRef CAS.
  16. See, for example, (a) K. C. Nicolaou, C. W. Hummel and Y. Iwabuchi, J. Am. Chem. Soc., 1992, 114, 3126 CrossRef CAS; (b) K. Higashi, S. Miyoshi, S. Nakabayashi, H. Yamada and Y. Ito, Chem. Pharm. Bull., 1992, 40, 2300 CAS; (c) T. Mukaiyama, T. Sasaki, E. Iwashita and K. Matsubara, Chem. Lett., 1995, 455 CAS; (d) J. Scheigetz, R. Zamboni, M. A. Bernstein and B. Roy, Org. Prep. Proced. Int., 1995, 27, 637 CAS; (e) J. Gervay and T. Q. Gregar, Tetrahedron Lett., 1997, 38, 5921 CrossRef CAS.
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