PURPOSE: To obtain a new fluorine-containing prostaglandin analog having excellent safety and durability of activity, useful as a prodrug of PGE0 and converted to the corresponding PGE0 by the hydrolysis in the body to exhibit bio-activity.

CONSTITUTION: The fluorine-containing prostaglandin analog expressed by the formula I [R1 is residue obtained by removing carboxyl group from carboxylic acid; R2 is H or residue obtained by removing OH from alcohol; R3 and R4 are H or OH-protecting group; R5 is (substituted) ≤10C hydrocarbon group], especially a compound expressed by the formula II, e.g. methyl-9- acetoxy-14-fluoro-11α,15S-dihydroxy-13,14-dihydroprost-8-en-1-oate. The compound of the formula I can be produced e.g. by reacting a 2-cyclopenten-1-one compound of the formula III with an alkyl metal compound.