Synlett 1990; 1990(6): 320-321
DOI: 10.1055/s-1990-21076
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Radical Cyclization of (Bromomethyl)dimethylsilyl Propargyl Ethers; VI. Serial Radical Cyclizations Leading to a Stereoselective Synthesis of Functionalized Diquinane Framework from an Acyclic Substrate1

Michel Journet* , William Smadja, Max Malacria
  • *Université Pierre et Marie Curie, Paris VI, Laboratoire de Chimie Organique de Synthèse, URA 408, Tour 44-54, 4 Place Jussieu, F-75252 Paris Cedex 05, France
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Publication History

Publication Date:
08 March 2002 (online)

Radical cyclization of 4-[(bromomethyl)dimethyl-siloxy)-2-methyl-1-undecene-5-yne in the presence of acrylonitrile leads stereoselectively by a radical reaction cascade to the diquinane system. This one-pot reaction allows the consecutive formation of four carbon-carbon bonds, with two contiguous quaternary centers and controls the stereoselective construction of four stereogenic centers.