Unsaturated ketones (7) were obtained in a reaction sequence involving BF3-mediated addition of the alkylaryl sulphone (3) and oxiranes (4), oxidation of the hydroxy group in the adducts, and elimination of arylsulphinic acid; the C-6 functionalization had a long-range effect on the steric course of reduction of the 15-oxo group in prostaglandin intermediates.
B. Achmatowicz, S. Marczak and J. Wicha, J. Chem. Soc., Chem. Commun., 1987, 1226 DOI: 10.1039/C39870001226
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