95303-88-1Relevant academic research and scientific papers
Conjugate Additions to α,β-Unsaturated Sulphoxides: Syntheses of Cyclopentenones and 9-Deoxyprostanoids
Brown, Peter J.,Jones, D. Neville,Khan, M. Akram,Meanwell, Nicholas A.,Richards, Pamela J.
, p. 2049 - 2060 (2007/10/02)
1,4-Dicarbonyl compounds, and hence cyclopentenone derivatives, were prepared by conjugate additions of enolate and related anions to α,β-unsaturated sulphoxides, followed by sulphoxide-ketone transformations.These transformations involved trapping the intermediate α-sulphinyl carbanions with dimethyl disulphide to give thioacetal monooxide derivatives, or Pummerer rearrangements of the sulphoxides to give alkenyl sulphides. 3-Substituted 2-ethoxycarbonylcyclopentenones prepared in this way were converted into 9-deoxyprostanoids and their 12-ethoxycarbonyl derivatives, the latter by use of 2-phenylsulphinyloct-1-en-3-one as an electrophilic prostanoid β-side-chain precursor.
