A New Synthesis of an Important Prostaglandin Intermediate by Selective Oxidation of a Trimethylsilylated Primary Alcohol to the Corresponding Aldehyde

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Abstract
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.