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Synlett 1993; 1993(8): 553-554
DOI: 10.1055/s-1993-22525
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A Concise Route to the Tetracyclic Skeleton of Stemodin

Philip Hegarty* , John Mann
  • *Department of Chemistry, Reading University, Whiteknights, Reading, P.O. Box 224, Reading RG6 2AD, England
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Publication History

Publication Date:
19 March 2002 (online)

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We describe a six stage synthesis of the tetracyclic skeleton of the diterpene stemodin. The key step involves a trimethylsilyl ketyl radical / nitrile cyclisation of 1, 1 - bis-cyanoethyl-2-tetralone (using a modification of the procedure originally reported by Corey) followed by functional group manipulation, and finally an acid catalysed intramolecuar aldol reaction.