Condensation of 4-bromophenacyl bromide (I) with phenol in the presence of potassium carbonate produced phenoxyacetophenone (II), which was cyclized to benzofuran (III) upon treatment with polyphosphoric acid in refluxing xylene. Suzuki coupling of (III) with 4-methoxybenzeneboronic acid (IV) gave the biphenyl benzofuran (V). The phenolic derivative (VI) was prepared by demethylation of ether (V) with boron tribromide. Lithiation of (VI) with n-butyllithium, followed by addition of N-methoxy-N-methyl benzamide afforded ketone (VII), which was converted to the benzyl benzofuran (VIII) by means of a modified Wolff-Kishner reduction. Coupling of (VIII) with methyl (S)-3-phenyllactate (IX) under Mitsunobu conditions furnished the corresponding ether (X). The methyl ester group of (X) was finally hydrolyzed with NaOH to yield the title carboxylic acid.

Condensation of 4-bromophenacyl bromide (I) with phenol in the presence of potassium carbonate produced phenoxyacetophenone (II), which was cyclized to benzofuran (III) upon treatment with polyphosphoric acid in refluxing xylene. Suzuki coupling of (III) with 4-methoxybenzeneboronic acid (IV) gave the biphenyl benzofuran (V). The phenolic derivative (VI) was prepared by demethylation of ether (V) with boron tribromide. Lithiation of (VI) with n-butyllithium, followed by addition of N-methoxy-N-methyl benzamide afforded ketone (VII), which was converted to the benzyl benzofuran (VIII) by means of a modified Wolff-Kishner reduction. Coupling of (VIII) with methyl (S)-3-phenyllactate (IX) under Mitsunobu conditions furnished the corresponding ether (X). The methyl ester group of (X) was finally hydrolyzed with NaOH to yield the title carboxylic acid.