The Oxidation of Some Steroidal Dienes and Trienes with Chromic Acid

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

James R. Hanson and Ismail Kiran


Abstract

The chromic acid oxidation of steroidal 2,4- and 3,5-dienes and 2,4,6-trienes is shown to take place at the secondary termini of the alkenes rather than at the allylic positions and is rationalized in terms of a sequence of 1:4-additions of chromic acid.


References

  1. For a review see: Encyclopedia of Reagents for Organic Synthesis, ed. L. A. Paquette, Wiley, Chichester, 1995, vol. 2, p. 1261 Search PubMed.
  2. L. R. Galagovsky and E. G. Gros, J. Chem. Res., 1993, (S)137; (M)0901 Search PubMed.
  3. G. J. Kent and E. S. Wallis, J. Org. Chem., 1959, 24, 1235 CrossRef CAS.
  4. E. J. Parish, S. A. Kizito and R. W. Heidepriem, Syth. Commun., 1993, 23, 223 Search PubMed.
  5. A. Nangia and A. Anthony, Synth. Commun., 1996, 26, 225 CrossRef CAS.
  6. M. Hector, R. W. Hattmann and V. C. O. Njar, Synth. Commun., 1996, 26, 1075 CrossRef CAS.
  7. W. G. Salmond, M. A. Barta and J. L. Havens, J. Org. Chem., 1978, 43, 2057 CrossRef CAS.
  8. M. L. Forcellese, I. Martucci and S. Calvitti, Gazz. Chim. Ital., 1983, 113, 737 CAS.
  9. K. Yasuda and H. Mori, Chem. Pharm. Bull. Jpn., 1967, 15, 179 CAS.
  10. K. Howden, I. M. Heilbron, E. R. H. Jones and B. C. L. Weedon, J. Chem. Soc., 1946, 39 RSC.
  11. J. R. Hanson and T. D. Organ, J. Chem. Soc., Perkin Trans. 1, 1970, 2473 RSC.
  12. M. M. Campbell, R. C. Craig, A. C. Boyd, I. M. Gilbert, D. S. Savage and T. Sleigh, J. Chem. Soc., Perkin Trans. 1, 1979, 3042 RSC.
  13. H. Laurent and R. Wiechert, Chem. Ber., 1968, 101, 2393 CAS.
  14. L. H. Knox, E. Velarde, S. Berger, D. Cuadriello, P. W. Landis and A. D. Cross, J. Am. Chem. Soc., 1963, 85, 1851 CrossRef CAS.
  15. D. Baldwin and J. R. Hanson, J. Chem. Soc., Perkin Trans. 1, 1972, 1889 RSC.