合成路线1

The reduction of 1,4-dihydroxy-9,10-anthraquinone (I) with NaBH4 in methanol gives 1,4-anthraquinone (II), which is reduced with Na2S2O4 in dioxane/water to yield 1,4-anthracenediol (III). The methylation of (III) with NaH and Me-I in DMF affords 1,4-dimethoxyanthracene (IV), which is condensed with 2-methoxy-1,4-benzoquinone (V) (obtained by oxidation of 2-methoxyhydroquinone (VI) with Ag2O and K2CO3 in benzene) by heating at 150 C with toluene in a sealed tube to provide the triptycene derivative (VII). The reaction of (VII) with KOH in dioxane/water gives the triptycenediol (VIII), which is oxidized with Ag2O in refluxing acetone to yield the triptycenequinone (IX). The bromination of (IX) with NBS in hot DMF affords the bromo derivative (X), which is finally oxidized with Ce(NH4)2(NO3)6 to afford the target triptycenediquinone.