Synthesis of biologically active β-substituted 4-(α- hydroxyalkyl)- and 4-(α-hydroxycycloalkyl)benzoic acids

Several novel compounds containing aromatic B-substituted alcohol fragment were obtained. Ring opening reactions of the 4-(2-metyl-2-oxyranyl)benzoic and 4-perhydro-1-benzoxyren-1-ylbenzoic acids with nucleophiles were used as key steps and led to the production of β-amino alcohols, β-nitro alcohols and vicinal diols. Maximal regioselectivity and product yields were obtained for the case when the reactant contained an isopropyl fragment. The obtained compounds possess a broad biological activity potential and are useful building-blocks in the synthesis physiologically active agents.