View PDF Version
 
DOI: 10.1039/A903641E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 1917-1926

Total synthesis of the cholesterol biosynthesis inhibitor 1233A via a (π-allyl)tricarbonyliron lactone complex

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

Roderick W. Bates, Eduardo Fernández-Megía, Steven V. Ley, Karola Rück-Braun and D. Matthew G. Tilbrook

Abstract

The total synthesis of the β-lactone cholesterol synthase inhibitor 1233A (1) is described employing the oxidative decomplexation of a (π-allyl)tricarbonyliron lactone (2) as the key synthetic step.

References

  1. (a) A. Pommier and J.-M. Pons, Synthesis, 1995, 729 CrossRef CAS; (b) C. Lowe and J. C. Vederas, Org. Prep. Proced. Int., 1995, 27, 307.
  2. D. C. Aldridge, D. Giles and W. B. Tuner, J. Chem. Soc. (C), 1971, 3888 RSC.
  3. S. Omura, H. Tomoda, H. Kumagai, M. D. Greenspan, J. B. Yodkovitz, J. S. Chen, A. W. Alberts, I. Martin, S. Mochales, R. L. Monaghan, J. C. Chabala, R. E. Schwartz and A. A. Patchett, J. Antibiot., 1987, 40, 1356 CAS.
  4. (a) H. Tomoda, H. Kumagai, Y. Takahashi, Y. Tanaka, Y. Iwai and S. Omura, J. Antibiot., 1988, 41, 247 CAS; (b) H. Tomoda, H. Kumagai, H. Tanaka and S. Omura, Biochim. Biophys. Acta, 1987, 922, 351 CAS.
  5. M. D. Greenspan, J. B. Yudkovitz, C. L. Lo, J. S. Chen, A. W. Alberts, V. M. Hunt, M. N. Chang, S. S. Yang, K. L. Thompson, Y. P. Chiang, J. C. Chabala, R. L. Monaghan and R. L. Schwartz, Proc. Natl. Acad. Sci. U.S.A., 1987, 84, 7488 CAS.
  6. (a) M. D. Greenspan, H. G. Bull, J. B. Yudkovitz, D. P. Hanf and A. W. Alberts, Biochem. J., 1993, 289, 889 CAS; (b) H. Nagashima, H. Kumagai, H. Tomoda and S. Omura, Life Sci., 1993, 52, 1595 CrossRef CAS.
  7. Y.-C. P. Chiang, M. N. Chang, S. S. Yang, J. C. Chabala and J. V. Heck, J. Org. Chem., 1988, 53, 4599 CrossRef CAS.
  8. (a) Y.-C. P. Chiang, S. S. Yang, J. V. Heck, J. C. Chabala and M. N. Chang, J. Org. Chem., 1989, 54, 5708 CrossRef CAS; (b) K. Mori and Y. Takahashi, Liebigs Ann. Chem., 1991, 1057 Search PubMed; (c) P. M. Wovkulich, K. Shankaran, J. Kiegiel and M. R. Uskokovic, J. Org. Chem., 1993, 58, 832 CrossRef CAS; (d) O. Dirat, C. Kouklovsky and Y. Langlois, J. Org. Chem., 1998, 63, 6634 CrossRef CAS.
  9. B. W. Dymock, P. J. Kocienski and J.-M. Pons, Synthesis, 1998, 1655 CrossRef CAS.
  10. (a) S. Wattanasin, H. D. Do, N. Bhongle and F. G. Kathawala, J. Org. Chem., 1993, 58, 1610 CrossRef CAS; (b) G. Guanti, L. Banfi and G. Schmid, Tetrahedron Lett., 1994, 35, 4239 CrossRef CAS.
  11. W. Adam, J. Baeza and J.-C. Liu, J. Am. Chem. Soc., 1972, 94, 2000 CrossRef CAS.
  12. S. V. Ley, L. R. Cox and G. Meek, Chem. Rev., 1996, 96, 423 CrossRef CAS.
  13. G. D. Annis, S. V. Ley, C. R. Self and R. Sivaramakrishnan, J. Chem. Soc., Perkin Trans. 1, 1981, 270 RSC.
  14. A. M. Horton, D. M. Hollinshead and S. V. Ley, Tetrahedron, 1984, 40, 1737 CrossRef CAS.
  15. R. W. Bates, R. Fernández-Moro and S. V. Ley, Tetrahedron, 1991, 47, 9929 CrossRef CAS.
  16. (a) J. K. Stille and B. L. Groh, J. Am. Chem. Soc., 1987, 109, 813 CrossRef CAS; (b) V. Farina, V. Krishnamurthy and W. J. Scott, Organic Reactions, ed. L. A. Paquette, John Wiley & Sons, New York, 1997,vol. 50, p. 1 Search PubMed.
  17. K. Mori and S. Senda, Tetrahedron, 1985, 41, 541 CrossRef CAS.
  18. A. S. Thompson, in Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, John Wiley & Sons, Chichester, 1995, vol. 3, p. 1957 Search PubMed.
  19. W. Clark-Still and C. Gennari, Tetrahedron Lett., 1983, 24, 4405 CrossRef CAS.
  20. E. Negishi, D. E. Van Horn and T. Yoshida, J. Am. Chem. Soc., 1985, 107, 6639 CrossRef CAS.
  21. E. Piers, T. Wong and K. A. Ellis, Can. J. Chem., 1992, 70, 2058 CAS.
  22. E. Piers, J. M. Chong and H. E. Morton, Tetrahedron, 1989, 45, 363 CrossRef CAS.
  23. T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 1980, 102, 5974 CrossRef CAS.
  24. (a) R. A. Johnson and K. B. Sharpless, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 7, p. 389 Search PubMed; (b) T. Katsuki and V. S. Martin, Organic Reactions, ed. L. A. Paquette, John Wiley & Sons, New York, 1996, vol. 48, p. 1 Search PubMed.
  25. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune and K. B. Sharpless, J. Am. Chem. Soc., 1987, 109, 5765 CrossRef CAS.
  26. S. V. Ley, J. Norman, W. P. Griffith and S. P. Marsden, Synthesis, 1994, 639 CrossRef.
  27. We thank Zeneca Pharmaceuticals and Merck for samples of the natural product 1233A.
  28. J. M. Behan, R. A. W. Johnstone and M. J. Wright, J. Chem. Soc., Perkin Trans. 1, 1975, 1216 RSC.
  29. H. Suzuki, T. Fuchita, A. Iwasa and T. Mishina, Synthesis, 1978, 905 CrossRef CAS.
  30. (a) G. A. Molander, Organic Reactions, ed. L. A. Paquette, John Wiley & Sons, New York, 1994, vol. 46, p. 211 Search PubMed; (b) P. Girard, J. L. Namy and H. B. Kagan, J. Am. Chem. Soc., 1980, 102, 2693 CrossRef CAS; (c) M. Matsukawa, T. Tabuchi, J. Inanaga and M. Yamaguchi, Chem. Lett., 1987, 2101 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.