Synthesis of 11beta-perfluorohexylestradiol

[reaction: see text] We report the synthesis of 11beta-perfluorohexylestradiol 1e using a perfluoroorganometallic reagent for the introduction of the fluorous part. This compound is useful for biological studies and for imaging the ERalpha estradiol receptor distribution in the whole cell by secondary ion mass spectrometry (SIMS). The key step of this synthesis involves the radical reduction of an 11beta-oxalate derivative. The stereochemical outcome of this reaction was studied for a range of C11 substituents, and we attempted to rationalize the apparent abnormal behavior of the phenyl group.