Opening of cyclohexene oxide (I) with pyrrolidine (II) in aqueous K2CO3 yielded the racemic trans-2-(1-pyrrolidinyl)cyclohexanol (III). Subsequent Mitsunobu coupling of (III) with phenol (IV) in the presence of DEAD and PPh3 produced ether (V). The intermediate acid chloride (VI) was then prepared by ester hydrolysis, followed by treatment with SOCl2.

Condensation of 4-(benzyloxy)benzaldehyde (VII) with N,N-dimethyl thioformamide (A) in the presence of LDA at -78 C generated the alpha-hydroxythioamide (VIII), which was cyclized by means of methanesulfonic acid to afford benzothiophene (IX). Friedel-Crafts acylation of (IX) with acid chloride (VI) upon heating in chlorobenzene yielded the 3-acyl benzothiophene (X). Subsequent displacement of the dimethylamino group of (X) by Grignard reagent (XI) produced the 2-aryl benzothiophene (XII). Deoxygenation of the keto group of (XII) was accomplished by the sequence of reduction to alcohol (XIII) with LiAlH4, followed by treatment with Et3SiH in trifluoroacetic acid to give (XIV). The benzyl ether of (XIV) was finally deprotected by hydrogenation over Pd/C to furnish the title compound.