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Synlett 1994; 1994(5): 335-336
DOI: 10.1055/s-1994-22844
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The First Synthesis of (±)-Taxodone

Anthony J. Sánchez* , Joseph P. Konopelski
  • *Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA
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Publication Date:
22 March 2002 (online)

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The total synthesis of (±)-taxodone (1) is described. The C-ring is formed by the cycloaddition of methyl acrylate with siloxyfuran 5 derived from isodrimenin (4). The C13 isopropyl group was introduced via a sulfur ylide rearrangement followed by reductive cleavage. Compound 1 was synthesized in 61% yield from diacetate 18 by deprotection and intramolecular oxirane opening with potassium t-butoxide and water in THF