View PDF Version
 
DOI: 10.1039/A700980A (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 1087-1090

Synthesis of tricholomenyn A and epitricholomenyn A by a palladium-catalysed β-halo enone coupling route

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

Andrew E. Graham and Richard J. K. Taylor

Abstract

The synthesis of tricholomenyn A is described via a route employing two palladium-catalysed Sonogashira coupling reactions; an efficient, stereoselective route to epitricholomenyn A is also reported.

References

  1. K. Kawazu, A. Kobayashi and K. Oe, Jap P, 0 341 075/ 1991(Chem. Abstr., 1991, 115, 181517k) Search PubMed; T. Nagata, Y. Ando and A. Hirrota, Biosci. Biotechnol. Biochem., 1992, 56, 810 Search PubMed.
  2. L. Garlaschelli, E. Magistrali, G. Vidari and O. Zuffardi, Tetrahedron Lett., 1995, 36, 5633 CrossRef CAS.
  3. I. Sattler, C. Gröne and A. Zeeck, J. Org. Chem., 1993, 58, 6583 CrossRef CAS and references cited therein.
  4. T. Higa, R. K. Okuda, R. M. Severns, P. J. Scheuer, C. H. He, X. Changfu and J. Clardy, Tetrahedron, 1987, 43, 1063 CrossRef CAS.
  5. B. Shen, Y. G. Whittle, S. J. Gould and D. A. Keszler, J. Org. Chem., 1990, 55, 4422 CrossRef CAS and references cited therein.
  6. L. Garlaschelli, G. Vidari and P. Vita-Finzi, Tetrahedron Lett., 1996, 37, 6223 CrossRef CAS.
  7. E. C. L. Gautier, N. J. Lewis, A. McKillop and R. J. K. Taylor, Tetrahedron Lett., 1994, 35, 8759 CrossRef CAS.
  8. L. Alcaraz, G. Macdonald, I. Kapfer, N. Lewis and R. J. K. Taylor, Tetrahedron Lett., 1996, 37, 6619 CrossRef CAS; I. Kapfer, N. J. Lewis, G. Macdonald and R. J. K. Taylor, Tetrahedron Lett., 1996, 37, 2101 CrossRef CAS.
  9. A. E. Graham, D. McKerrecher, D. H. Davies and R. J. K. Taylor, Tetrahedron Lett., 1996, 37, 7445 CrossRef CAS.
  10. J. K. Stille and J. H. Simpson, J. Am. Chem. Soc., 1987, 109, 2138 CrossRef CAS for a review, see T. N. Mitchell, Synthesis, 1992, 803 Search PubMed.
  11. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 4467 CrossRef CAS; for a recent review, see I. B. Campbell, in Organocopper Reagents; A Practical Approach, ed. R. J. K. Taylor, Oxford University Press, Oxford, 1994, ch. 10 Search PubMed.
  12. T. Kamikubo and K. Ogasawara, Chem. Commun., 1996, 1679 RSC.
  13. B. P. Warner and S. L. Buchwald, J. Org. Chem., 1994, 59, 5822 CrossRef CAS.
  14. F. Bosse, A. R. Tundoori, A. J. Niestroj, O. Gronwald and M. E. Maier, Tetrahedron, 1996, 52, 9485 CrossRef CAS and references cited therein.
  15. E. C. L. Gautier, A. E. Graham, A. McKillop, S. P. Standen and R. J. K. Taylor, Tetrahedron Lett., 1997, 38, in press: A. Cornélis, P. Laszlo and M. W. Zettler, Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, Chichester, 1995, p. 3667 Search PubMed.
  16. D. McKerrecher, D. H. Davies and R. J. K. Taylor, unpublished results.
Click here to see how this site uses Cookies. View our privacy policy here.