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Synlett 1992; 1992(10): 821-822
DOI: 10.1055/s-1992-21504
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Regio- and Stereoselective Cyanation of Aromatic Steroids in the 9α- and 12α-Position by DDQ-TMSCN

Alain Guy* , Joël Doussot, Jean-Paul Guetté, Robert Garreau, Marc Lemaire
  • *Laboratoire de Chimie Organique (URA 1103), Conservatoire National des Arts et Métiers 292, rue Saint-Martin, F-75141 Paris Cédex 03, France
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Publication Date:
08 March 2002 (online)

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Aromatic steroids are oxidized by DDQ to generate the corresponding cationic species, which in turn react with TMSCN to afford the 9α-cyano products in a one pot procedure. The same substrates after their transformation into Δ9-11 steroids by DDQ are regio- and stereoselectively cyanated 12α-position.

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