Jones oxidation of 4-bromothiophene-2-carbaldehyde (I) leads to acid (II), which is further esterified with H2SO4/MeOH to furnish methyl 4-bromothiophene-2-carboxylate (III). Subsequent Heck coupling of aryl bromide (III) with cyclohexylammonium acrylate (IV) gives rise to the thienylacrylic acid (V). Cyclization of (V) with SOCl2 in the presence of pyridine produces the thienothiophene derivative (VI). Acid chloride (VI) is then coupled to N-(dimethylaminopropyl)aniline (VII) under Schotten-Baumann conditions, yielding amide (VIII). Finally, photochemical cyclization of (VIII) affords the target tetracyclic compound.