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Synthesis 1989; 1989(12): 940-942
DOI: 10.1055/s-1989-27437
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Direct Oxidation of Alkyl Trimethyl- and Triethylsilyl Ethers to Carbonyl Compounds. Application to Synthesis of Prostanoids

G. A. Tolstikov* , M. S. Miftakhov, M. E. Adler, N. G. Komissarova, O. M. Kuznetsov, N. S. Vostrikov
  • *Institute of Chemistry, Bashkirian Research Centre, USSR Acad. Sci. Ural Department, Ufa, SU-450054, USSR
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Publication Date:
02 May 2002 (online)

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Direct oxidation of (-)-7α-triethylsiloxy-6β-triethylsiloxymethyl-3 -oxo-cis-2-oxabicyclo[3.3.0]octane with the Swern reagent proceeds selectively to afford (-)-7α-triethylsiloxy-6β-formyl-3-oxo-cis-2 -oxabicyclo[3.3.0]octane. Condensation of this aldehyde with dimethyl 2 -oxoheptylphosphonate under phase-transfer conditions gives (-)-7α -triethylsiloxy-3-oxo-6β-[3-oxo-1(E)-octenyl]-cis-2-oxabicyclo[3.3.0] octane which, on acidic hydrolysis, is converted into the known prostaglandine synthetic intermediate (-)-7α-hydroxy-3-oxo-6β-[3-oxo-1(E) -octenyl]-cis-2-oxabicyclo[3.3.0]octane.