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

Article abstract of DOI:10.1055/s-1987-28151

The bis(trimethylsilyl) 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 35-40percent in a convenient one-pot procedure.