[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C@@H:12]([OH:23])[CH2:11][C@H:10]1[OH:24].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C.O>CC(C)=O.C(OCC)C>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@H:9]1[C:10](=[O:24])[CH2:11][C@H:12]([OH:23])[C@@H:13]1[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]PGF2α, 15-(tetrahydropyranyl ether) (2 g.) in acetone (75 ml.) is cooled to -45° C. and thereafter treated with 1.2 ml. of the Jones reagent. The mixture is stirred for 30 min. at -35° to -45° C. and thereafter treated with 0.5 ml. of isopropanol and stirred an additional 15 min. The reaction mixture is then poured into a mixture of ice, water, and diethyl ether. The mixture is then extracted with diethyl ether and the combined ethereal extracts washed with brine, and dried over sodium sulfate. After filtration removal of solvent proceeds by rotary evaporation. Crude product (1.8 g.) thereby obtained is chromatographed on 360 g. of acid washed silica gel eluting with 45 percent ethyl acetate in hexane. PGD2, 15-(tetrahydropyranyl ether) (800 mg.) is thereby obtained.
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