stirred for 2 hours treated with 2 n aqueous sodium sulfite 20 ml washed successively with 5 aqueous sodium bicarbonate and 5 aqueous sodium chloride dried and concentrated to yield 2 95 g of crude 9 deoxy 6 9 u03b1 epoxy 5 iodo 14 bromo pgf 1 u03b1 methyl ester a 0 13 g aliquot of crude product is chromatographed on 13 g of acid washed silica gel eluting with ethyl acetate and benzene 3 7 to yield 0 088 g of pure formula xxxii product nmr absorptions are observed at 0 89 1 1 3 18 3 66 3 6 4 8 and 5 88 u03b4 the mass spectrum for the trimethylsilyl derivative exhibits a high resolution peak at 701 1183 a molecular ion at 716 and other peaks at 645 637 589 547 529 510 and 173 infrared absorptions are observed at 3380 1740 1655 1230 1170 1080 and 1050 cm 1 b the reaction product of part a 1 0 g of crude unchromatographed product in methylene chloride 10 ml is treated with dihydropyran 3 ml and a 3 ml solution of methylene chloride saturated with pyridine hydrochloride after 20 hours the resulting mixture is then diluted with diethyl ether washed successively with 5 aqueous sodium bicarbonate and 5 aqueous sodium chloride dried and concentrated to a 1 12 g residue of 9 deoxy 6 9 u03b1 epoxy 5 iodo 14 bromo pgf 1 u03b1 methyl ester 11 15 bis tetrahydropyranol ether nmr absorptions are observed at 0 9 1 05 2.