Synthesis of the functionalised core of neoliacinic acid

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

J. Stephen Clark, Alexander G. Dossetter, Alexander J. Blake, Wan-Sheung Li and William G. Whittingham


Abstract

An advanced intermediate in the synthesis of neoliacinic acid has been prepared, and the structure and relative stereochemistry have been confirmed by X-ray crystallography.


References

  1. D. Takaoka, H. Nozaki and M. Nakayama, J. Chem. Soc., Chem. Commun., 1987, 1861 RSC.
  2. J. Jakupovic, V. Castro and F. Bohlmann, Phytochemistry, 1987, 26, 2011 CrossRef CAS.
  3. N. Gören, J. Jakupovic and S. Topal, Phytochemistry, 1990, 29, 1467 CrossRef CAS.
  4. H. Nozaki, M. Hiroi, D. Takaoka and M. Nakayama, J. Chem. Soc., Chem. Commun., 1983, 1107 RSC.
  5. J. S. Clark, A. G. Dossetter and W. G. Whittingham, Tetrahedron Lett., 1996, 37, 5605 CrossRef CAS.
  6. B. A. Narayanan and W. H. Bunnelle, Tetrahedron Lett., 1987, 28, 6261 CrossRef CAS; T. V. Lee, J. A. Channon, C. Cregg, J. R. Porter, F. S. Roden and H. T.-L. Yeoh, Tetrahedron, 1989, 45, 5877 CrossRef CAS.
  7. T. J. Mickelson, J. L. Koviach and C. J. Forsyth, J. Org. Chem., 1996, 61, 9617 CrossRef CAS.
  8. D. Grafstein, J. Am. Chem. Soc., 1955, 77, 6650 CrossRef CAS.
  9. D. V. C. Awang and S. Wolfe, Can. J. Chem., 1969, 47, 706 CAS.
  10. D. Y. Jackson, Synth. Commun., 1988, 18, 337 CAS.
  11. F. Sato, Y. Kobayashi, O. Takahashi, T. Chiba, Y. Takeda and M. Kusakabe, J. Chem. Soc., Chem. Commun., 1985, 1636 RSC.
  12. A. M. Dennis, J. D. Korp, I. Bernal, R. A. Howard and J. L. Bear, Inorg. Chem., 1983, 22, 1522 CrossRef CAS.
  13. J. Adams, M.-A. Poupart, L. Grenier, C. Schaller, N. Ouimet and R. Frenette, Tetrahedron Lett., 1989, 30, 1749 CrossRef CAS.
  14. For examples of the stereoselective addition of AlMe3 to cyclic ketones, see: E. C. Ashby and J. T. Laemmle, Chem. Rev., 1975, 75, 521 Search PubMed; K. C. Nicolaou, M. E. Duggan and C.-K. Hwang, J. Am. Chem. Soc., 1989, 111, 6666 CrossRef CAS.
  15. For examples of the synthesis of bicyclic ethers by [1,2]-shifts of oxonium ylides generated from carbenoids, see: F. G. West, T. H. Eberlein and R. W. Tester, J. Chem. Soc., Perkin Trans. 1, 1993, 2857 Search PubMed.
  16. R. Annunziata, M. Cinquini, F. Cozzi, C. Gennari and L. Raimondi, J. Org. Chem., 1987, 52, 4674 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.