合成路线1

The Diels-Alder cycloaddition between 1,4-dimethoxyanthracene (IV) and methoxyhydroquinone (V) in the presence of Ag2O and ZnI2 yields the triptycene quinone (VI). This compound has also been obtained by stepwise oxidation of (V) to methoxybenzoquinone (VII) with Ag2O, followed by Diels-Alder condensation with 1,4-dimethoxyanthracene (IV) to produce adduct (VIII) as a mixture of two stereoisomers. After isomerization of ketones (VIII) with KOH, oxidation with Ag2O leads to quinone (VI). Mono-quinone (VI) is oxidized to the bis-quinone (IX) employing ceric ammonium nitrate. Then, regioselective bromination of (IX) with N-bromosuccinimide (NBS) furnishes bromoquinone (X). Alternatively, compound (XI) is obtained from the bromination of (VI) with NBS, followed by oxidation with ceric ammonium nitrate). When bis-quinone (X) in THF solution is treated with dimethylamine gas (containing small amounts of methylamine), the title compound is obtained a regioisomeric mixture of methylamino derivatives, along with the expected dimethylamino analogues, which are separated by column chromatography.