Steroid A-Ring Aromatisation of C-Ring Substituted 1,4-dien-3-ones

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James J. Harburn, Gabrielle C. Loftus and Brian A. Marples


Abstract

A number of A-ring steroidal 1,4-dien-3-ones 7, 8, 9 and 10 have been aromatised in zinc/pyridine–water; the products depend upon the position and type of C-ring substituents and provide new evidence in support of a radical anion mechanism.


References

  1. For a review see D. N. Kirk and M. P. Hartshorn, Steroid Reaction Mechanisms, Elsevier, Amsterdam, 1968, p. 277 Search PubMed.
  2. J. H. Brewster, J. Am. Chem. Soc., 1954, 76, 6361, 6364 CrossRef CAS.
  3. J. J. Harburn, G. C. Loftus and B. A. Marples, Tetrahedron, 1998, in press Search PubMed.
  4. K. Tsuda, S. Nozoe and K. Ohata, Chem. Pharm. Bull., 1963, 11, 1265 CAS.
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