View PDF Version
 
DOI: 10.1039/A704413E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 3501-3508

Improved procedure for Juliá–Colonna asymmetric epoxidation of α,β-unsaturated ketones: total synthesis of diltiazem and Taxol[hair space]TM side-chain

(Note: The full text of this document is currently only available in the PDF Version )

Brian M. Adger, James V. Barkley, Sophie Bergeron, Michael W. Cappi, Benjamin E. Flowerdew, Mark P. Jackson, Ray McCague, Thomas C. Nugent and Stanley M. Roberts

Abstract

Poly-L-leucine catalyses the asymmetric epoxidation of enones 1–6 efficiently in a non-aqueous medium to provide the epoxy ketones 7–12 (70–91% yield; 80 to [greater than or equal, slant]95% ee). The strategy was used to make diltiazem 16 and the Taxol[hair space]TM side chain 23 in single enantiomer form.

References

  1. M. Bougauchi, S. Watanabe, T. Arai, H. Sasai and M. Shibasaki, J. Am. Chem. Soc., 1997, 119, 2329 CrossRef CAS.
  2. C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald and P. J. Murray, Angew. Chem., Int. Ed. Engl., 1997, 36, 410 CrossRef CAS.
  3. W. Kroutil, P. Mayon, M. E. Lasterra-Sánchez, S. J. Maddrell, S. M. Roberts, S. R. Thornton, C. J. Todd and M. Tüker, Chem. Commun., 1996, 845 RSC and references cited therein.
  4. For a preliminary communication of this work see: P. A. Bentley, S. Bergeron, M. W. Cappi, D. E. Hibbs, M. B. Hursthouse, T. C. Nugent, R. Pulido, S. M. Roberts and L. E. Wu, Chem. Commun., 1997, 739 Search PubMed.
  5. (a) H. Heaney, Aldrichim. Acta, 1993, 26, 35 Search PubMed; (b) M. S. Cooper, H. Heaney, A. J. Newbold and W. R. Sanderson, Synlett, 1990, 533 CrossRef.
  6. S. Itsuno, M. Sakakura and K. Ito, J. Org. Chem., 1990, 55, 6047 CrossRef CAS.
  7. (a) O. Miyata, T. Shinada, I. Ninomiya and T. Naito, Tetrahedron, 1997, 53, 2421 CrossRef CAS; (b) J. A. Vega, S. Cueto, A. Ramos, J. J. Vaquero, J. L. Garcia-Navio, J. Alvarez-Builla and J. Ezquerra, Tetrahedron Lett., 1996, 37, 6413 CrossRef CAS; (c) S. B. Desai, N. P. Argade and K. N. Ganesh, J. Org. Chem., 1996, 61, 6730 CrossRef CAS; (d) A. Nangia, P. B. Rao and N. N. L. Madhavi, J. Chem. Res., 1996, 312 Search PubMed; (e) E. N. Jacobsen, L. Deng, Y. Furukawa and L. E. Martinez, Tetrahedron, 1994, 50, 4323 CrossRef CAS; (f) L. T. Kanerva and O. Sundholm, J. Chem. Soc., Perkin Trans. 1, 1993, 1385 RSC; (g) A. Schwartz, P. B. Madan, E. Mohacsi, J. P. O'Brien, L. J. Todaro and D. L. Coffen, J. Org. Chem., 1992, 57, 851 CrossRef CAS; (h) C. Giordano, A. Restelli and M. Villa, J. Org. Chem., 1991, 56, 2270 CrossRef CAS; (i) K. G. Watson, Y. M. Fung, M. Gredley, G. J. Bird, W. R. Jackson, H. Gountzos and B. R. Matthews, J. Chem. Soc., Chem. Commun., 1990, 1018 RSC; (j) B. Kojić-Prodić, Z. Ružić-Toroš, V. Šunjić, E. Decorte and F. Moimas, Helv. Chim. Acta, 1984, 67, 916 CrossRef CAS; (k) T. Hashiyama, H. Inoue, M. Konda and M. Takeda, J. Chem. Soc., Perkin Trans. 1, 1984, 1725 RSC.
  8. J. R. Flisak, K. J. Gombatz, M. M. Holmes, A. A. Jarmas, I. Lantos, W. L. Mendelson, V. J. Novack, J. J. Remich and L. Snyder, J. Org. Chem., 1993, 58, 6247 CrossRef CAS.
  9. (a) G. Bellucci, G. Catelani, C. Chiappe and F. D'Andrea, Tetrahedron Lett., 1994, 35, 8433 CrossRef CAS; (b) P. W. Baures, D. S. Eggleston, J. R. Flisak, K. Gombatz, I. Lantos, W. Mendelson and J. J. Remich, Tetrahedron Lett., 1990, 31, 6501 CrossRef CAS.
  10. R. P. Srivastava, J. K. Zjawiony, J. R. Peterson and J. D. McChesney, Tetrahedron: Asymmetry, 1994, 5, 1683 CrossRef CAS.
  11. J.-N. Denis, A. Correa and A. E. Greene, J. Org. Chem., 1990, 55, 1957 CrossRef CAS.
  12. L. Deng and E. N. Jacobsen, J. Org. Chem., 1992, 57, 4320 CrossRef CAS.
  13. G. Li, H.-T. Chang and K. B. Sharpless, Angew. Chem., Int. Ed. Engl., 1996, 35, 451 CrossRef CAS.
  14. J.-N. Denis, A. M. Kanazawa and A. E. Greene, Tetrahedron Lett., 1994, 35, 105 CrossRef CAS.
  15. M. Takeshita and N. Akutsu, Tetrahedron: Asymmetry, 1992, 3, 1381 CrossRef CAS.
  16. Structure Solution Methods: MITHRIL, C. J. Gilmore, MITHRIL—an integrated direct methods computer program, J. Appl. Cryst., 1984, 17, 42, University of Glasgow, Scotland, ( 1984) Search PubMed; DIRDIF, P. T. Beurskens, DIRDIF: Direct Methods for Difference Structures—an automatic procedure for phase extension and refinement of difference structure factors. Technical Report 1984/1 Crystallography Laboratory, Toernooiveld, 6525 Ed Nijmegen, Netherlands.
  17. Least-squares: function minimised: Σw(|Fo| – |Fc|)2, where: w= 4Fo2/σ2(Fo2), σ2(Fo2)=[S2(C+R2B)+(pFo2)2]/Lp2, S= scan rate, C= total integrated peak count, R= ratio of scan time to background counting time, B= total background count, Lp= Lorentz-polarization factor, p=p-factor.
  18. Standard deviation of an observation of unit weight: [Σw(|Fo| – |Fo|)2/(No–Nv)]½, where: No= number of observations, Nv= number of variables.
  19. D. T. Cromer and J. T. Waber, International Tables for X-ray Crystallography, The Kynoch Press, Birmingham, England, 1974, vol. IV, Table 2.2A Search PubMed.
  20. J. A. Ibers and W. C. Hamilton, Acta Crystallogr., 1964, 17, 781 CrossRef.
  21. D. T. Cromer, International Tables for X-ray Crystallography, The Kynoch Press, Birmingham, England, 1974, vol. IV, Table 2.3.1 Search PubMed.
  22. TEXSAN, TEXRAY Structure Analysis Package, Molecular Structure Corporation, 1985.
Click here to see how this site uses Cookies. View our privacy policy here.