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Synthesis 1987; 1987(11): 1012-1013
DOI: 10.1055/s-1987-28151
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A New Synthesis of an Important Prostaglandin Intermediate by Selective Oxidation of a Trimethylsilylated Primary Alcohol to the Corresponding Aldehyde

Rainer Mahrwald* , Fritz Theil, Hans Schick, Hans-Joachim Palme, Heidrun Nowak, Gisela Weber, Sigfrid Schwarz
  • *Central Institute of Organic Chemistry of the Academy of Sciences of the GDR, Rudower Chaussee 5, DDR-1199 Berlin, German Democratic Republic
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Publication Date:
12 September 2002 (online)

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The bis(trimethysilyl) ether of the prostaglandin precursor rac-3 was oxidized with high selectivity to the trimethylsilylated Corey aldehyde rac-1f using Collins reagent (chromium(VI) oxide/pyridine) in dichloromethane. This unstable compound was subjected without isolation to a twophase Horner olefination by adding the dimethyl phosphonate 4 and concentrated aqueous sodium hydroxide to the oxidation mixture. Thus, the prostaglandin intermediate rac-5 was obtained in a yield of 35-40% in a convenient one-pot procedure.