A solution of 500 mg of (±)-11-deoxyprostaglandin Ei was dissolved in 30 ml of methanol and solid sodium borohydride was added portionwise until no more starting material could be detected by tic analysis (40% ethyl acetate-60% hexane). The reaction solution was poured into water and extracted with ethyl acetate. The organic phase was washed with brine and dried over anhydrous sodium sulfate. The solvent was eliminated under reduced pressure and the residue purified via preparative tic to yield 303 mg of (±)-11-deoxyprostaglandin Fia methyl ester and 98 mg of its 9/3 epimer. Basic hydrolysis of these compounds in the usual manner yielded (±)-ll-deoxyprostaglandin Fia [mp 97-98.5°; ir 3400 (br), 3160 (br), 2970 (sh), 2930 (s), 2860 (sh), 1695 (s), 9.75 (s) cm'1; nmr 2.31 (t, / = 7 Hz, CH,CO), 4.00-4.30 (m, 2 H, CHOH), 5.
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