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Synlett 1990; 1990(11): 663-665
DOI: 10.1055/s-1990-21201
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Expedient Construction of the Dicyclopenta[a,d]cyclooctene Core of Ceroplastin Di- and Sesterterpenes

Leo A. Paquette* , Shaowo Liang, Paul Galatsis
  • *Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA
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Publication Date:
08 March 2002 (online)

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A fully stereocontrolled anionic oxy-Cope rearrangement is illustrated to be effective for the assembly of tricycle 13 containing the dicyclopenta[a,d]cyclooctene ring system with cis B/C ring fusion stereochemistry. Preliminary three-step conversion of 2-methylcyclopentanone to 1-bromo-2-methylcyclopentene (11) and formation of 1,4-dimethyl-8-methylenebicyclo[3.2.1]oct-3-en-2-one (7) from 1,3-dimethyl-1,3-cyclohexadiene in only 4 steps sets the stage for this remarkably rapid enhancement of structural complexity.

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