Abnormal Beckmann fragmentation/ring closing metathesis route for preparation of 18-nor-Δ13(17)-androgens and their 18-nor-13,17-epoxide derivatives

Cunde Wang, Nigam P. Rath, Douglas F. Covey

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

The synthesis of 18-nor-Δ13(17)-androgens and the structurally related 13,17-epoxides is described. The synthetic route involves the cleavage of 17-ketosteroids by an abnormal Beckmann rearrangement, modification of the D-ring cleavage product to obtain an intermediate tricyclic diene and ring closing metathesis of the diene to the 18-nor-Δ13(17)-androgen. (3α,5α)-18-Norandrost-13(17)-en-3-ol and the derivative 13α,17α- and 13β,17β-epoxides were prepared by this route.

Original languageEnglish
Pages (from-to)7837-7839
Number of pages3
JournalTetrahedron Letters
Volume47
Issue number45
DOIs
StatePublished - Nov 6 2006

Keywords

  • 18-Nor-13,17-epoxysteroids
  • 18-Nor-Δ-steroids
  • Abnormal Beckmann rearrangement
  • Neurosteroids
  • Olefin metathesis

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