Liquid phase diastereoselective hydrogenation of a prostaglandin-F intermediate has been studied over two commercial 5% Pt/Al2O3 catalysts. More specifically, the effect of metal dispersion and pore diameter on the reaction, as well as the conditions which allow to improve the diastereoselectivity and eventually orient towards the synthesis of the natural-like compound have been examined. The catalysts were characterized by nitrogen sorption isotherms, XRD, Hn-chemisorption, and XPS. It has been found that the characteristics of the catalysts (especially the textural properties) and the nature of the solvent strongly influence the catalytic behavior. In the presence of acetic acid as a solvent, it is possible to direct the formation of allylic alcohol to the (11S,15S) configuration which corresponds to the natural-like diastereoisomer compound.