Pyridine, hydrofluoride (1:1) → methyl(11R,12S,13E)-9-butyryloxy-11,15-dihydroxy-16,16,20-trimethyl-7-thiaprosta-8,13-dienoate

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Using as the materials a hydrogen fluoride-pyridine solution (0.25 ml) and methyl(11R,12S,13E)-9-butyryloxy-11-tert-butyldimethylsiloxy-15-hydroxy-16,16,20-trimethyl-7-thiaprosta-8,13-dienoate (100 mg), the same procedure as in Example 2 was performed to separately obtain two stereoisomers of methyl(11R,12S,13E)-9-butyryloxy-11,15-dihydroxy-16,16,20-trimethyl-7-thiaprosta-8,13-dienoate different at the 15-position. (Low polarity compound: 26 mg, 33%; high polarity compound: 28 mg, 35%)

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