View PDF Version
 
DOI: 10.1039/A809823I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 839-842

Total synthesis of the polyenoyltetramic acid mycotoxin erythroskyrine[hair space]†

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

Darren J. Dixon, Steven V. Ley, Tibor Gracza and Peter Szolcsanyi

Abstract

The first total synthesis of erythroskyrine, a polyenoyltetramic acid mycotoxin and principal pigment of Penicillium Islandicum Sopp., is described using a palladium(II) catalysed oxycarbonylation to create the furan-derived bicyclic portion 3 and the phosphonate ester 5 to furnish both the polyenoyl chain and the N-methyl(S[hair space])-valine derived tetramic acid terminus.

References

  1. For an excellent review see B. J. L. Royles, Chem. Rev., 1995, 95, 1981 Search PubMed and references cited therein.
  2. B. H. Howard and H. Raistrick, Biochem. J., 1949, 44, 227 CAS.
  3. B. H. Howard and H. Raistrick, Biochem. J., 1954, 57, 212 CAS.
  4. (a) J. Shoji and S. Shibata, Chem. Ind., 1964, 419 Search PubMed; (b) J. Shoji, S. Shibata, U. Sankawa, H. Taguchi and Y. Shibanuma, Chem. Pharm. Bull., 1965, 13, 1240 CAS.
  5. J. A. Beutler, B. D. Hilton, P. Clark, M. S. Tempesta and D. G. Corley, J. Nat. Prod., 1988, 51, 562 CrossRef CAS.
  6. R. C. F. Jones and M. Tankard, J. Chem. Soc., Chem. Commun., 1990, 765 RSC.
  7. R. Rossin, P. R. Jones, P. J. Murphy and W. R. Worsley, J. Chem. Soc., Perkin Trans. 1, 1996, 1323 RSC.
  8. (a) J. R. McDermott and N. L. Benoiton, Can. J. Chem., 1973, 51, 1915 CAS; (b) R. C. F. Jones and G. E. Peterson, Tetrahedron Lett., 1983, 24, 4751 CrossRef CAS.
  9. S. V. Ley and P. R. Woodward, Tetrahedron Lett., 1987, 28, 345 CrossRef CAS.
  10. (a) M. E. Jung and L. A. Light, Tetrahedron Lett., 1982, 23, 3851 CrossRef CAS; (b) R. Lenz and S. V. Ley, J. Chem. Soc., Perkin Trans. 1, 1997, 3291 RSC.
  11. (a) A. L. Raymond and E. F. Schroeder, J. Am. Chem. Soc., 1948, 70, 2785 CrossRef CAS; (b) P. J. Garegg and B. Samuelson, J. Chem. Soc., Perkin Trans. 1, 1980, 2866 RSC; (c) M. Kleban, Dissertation, Universität Stuttgart, 1996 Search PubMed; (d) T. Hasenöhrl, Dissertation, Universität Stuttgart, 1996 Search PubMed.
  12. (a) T. Hasenöhrl, U. Stahl, T. Gracza, A. Lieberknecht and V. Jäger, Synthesis, in press Search PubMed; (b) W. Frey, T. Gracza, T. Hasenöhrl, A. Lieberknecht and V. Jäger, Z. für Kristal, in press Search PubMed.
  13. K. Omura and D. Swern, Tetrahedron, 1978, 34, 1651 CrossRef CAS.
  14. K. Takai, K. Nitta and K. Utimoto, J. Am. Chem. Soc., 1986, 108, 7408 CrossRef CAS.
  15. We are very grateful to Neil Feeder of the Department of Chemistry, Cambridge, UK for determination of the single crystal X-ray structure.
  16. R. N. Lacey, J. Chem. Soc., 1954, 850 RSC.
  17. J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.