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Synlett 1992; 1992(10): 809-810
DOI: 10.1055/s-1992-21500
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Tandem Ring Expansion-Cyclisation Reactions: A Novel Method for the Rapid Construction of the Bicyclo[5.3.0]decane Ring System

Kevin I. Booker-Milburn*
  • *Departments of Chemistry, University of Salford, Salford, M5 4WT and University of Reading, Whiteknights, P. O. Box 224, Reading, Berks., RG26 2AD, England
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Publication Date:
08 March 2002 (online)

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Treatment of the cyclopropyl silyl ether 6 with ferric chloride in DMF gave the 5,7-bicyclic chloro ketone 8 via a tandem free radical ring expansion-cyclisation sequence. The acetylenic derivatives 13 and 18 underwent the same expansion-cyclisation sequence to yield similar 5,7-carbocycles.