Synthesis of the eight possible optically active isomers of 2-(4-(2-hydroxycyclopentylmethyl)phenyl)propionic acid.

A recently synthesized compound, (±)-2-[4-(2-oxocyclopentylmethyl) phenyl] propionic acid, had good anti-inflammatory and analgesic activities. One of the metabolites of this compound showed more potent prostaglandin synthetase inhibitory activity than the parent acid. For the structural determination and absolute configurational assignment of the metabolites, we synthesized the eight possible title alcohols and carried out stereochemical assignment of these alcohols.