[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].C(=O)([O-])O.[Na+].C(OC(=O)C)C.CCCCCC>CC(C)=O.C(OCC)(=O)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]14 4 mg of PGF2 α body (q) was dissolved in 0.8 ml of acetone in a 5 ml test tube and 12.4 μl of Jones reactant (2.4M) was added to the solution dropwise with a syringe at -30° C. in a stream of argon. The mixture was stirred at -30° C. for 30 minutes and then diluted with 1 ml of ethyl acetate. After 1 ml of a saturated aqueous solution of sodium hydrogencarbonate was added, the mixture was agitated vigorously. When the color of the aqueous layer shaded into green, 10 ml of ethyl acetate and 10 ml of a saturated aqueous solution of sodium hydrogen-carbonate were further added and the mixture was agitated vigorously. The organic layer and the aqueous layer were extracted with two 10 ml portions of ethyl acetate. The extract and the organic layer were dried together over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography over silica gel (1.4 g of silica gel manuf. by Merck; ethylacetate-hexane=1:3) to obtain 13.1 mg (91% yield) of PGD2 body (s).
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