Synthesis of endo,exo-furofuranones using a highly diastereoselective C–H insertion reaction

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

Richard C. D. Brown


Abstract

A highly stereoselective ring closure of α-diazo-γ-butyrolactones to form the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane ring system is reported; a formal synthesis of the furofuran lignan asarinin 1 is also described.


References

  1. R. S. Ward, Nat. Prod. Rep., 1995, 12, 183 RSC.
  2. R. S. Ward, Nat. Prod. Rep., 1997, 14, 43 RSC.
  3. R. S. Ward, Chem. Soc. Rev., 1982, 75 RSC.
  4. C. Schmit, J. B. Falmangne, J. Escudero, H. Vanlierde and L. Ghosez, Org. Synth., 1990, 69, 199.
  5. O. Mårtensson and E. Nilsson, Acta Chem. Scand., 1960, 1129 CAS.
  6. H. C. Arndt and S. A. Carroll, Synthesis, 1979, 202 CrossRef CAS.
  7. E. J. Corey, Z. Arnold and J. Hutton, Tetrahedron Lett., 1970, 307 CrossRef.
  8. A. Schmitz, U. Kraatz and F. Korte, Chem. Ber., 1975, 108, 1010 CAS.
  9. M. D. Weingarten and A. Padwa, Synlett, 1997, 189.
  10. D. F. Taber, K. You and Y. Song, J. Org. Chem., 1995, 60, 1093 CrossRef CAS.
  11. L. Lombardo and L. N. Mander, Synthesis, 1980, 368 CrossRef CAS.
  12. D. A. Evans, T. C. Britton, J. A. Ellman and R. L. Dorow, J. Am. Chem. Soc., 1990, 112, 4011 CrossRef CAS.
  13. S. E. Denmark, N. Chatani and S. V. Pansare, Tetrahedron, 1992, 48, 2191 CrossRef CAS.
  14. S. Takano, K. Samizu and K. Ogasawara, Synlett, 1993, 785 CrossRef CAS.
  15. K. Samizu and K. Ogasawara, Chem. Lett., 1995, 543.
  16. D. R. Stevens and D. A. Whiting, Tetrahedron Lett., 1986, 27, 4629 CrossRef CAS.
  17. D. R. Stevens, C. P. Till and D. A. Whiting, J. Chem. Soc., Perkin Trans. 1, 1992, 185 RSC.
  18. C. P. Till and D. A. Whiting, J. Chem. Soc., Chem. Commun., 1984, 590 RSC.
  19. A. Pelter, R. S. Ward, P. Collins, R. Venkateswarlu and I. T. Kay, J. Chem. Soc., Perkin Trans. 1, 1985, 587 RSC.
  20. J. S. Buck and W. H. J. Perkin, J. Chem. Soc., 1924, 125, 1680 Search PubMed.
  21. D. A. Fletcher, R. F. McMeeking and D. Parkin, J. Chem. Inf. Comput. Sci., 1996, 36, 746 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.