We report the total synthesis of phenanthroviridin aglycon with interesting antibacterial and anticancer activities. A Pd-catalyzed direct arylation of 5-hydroxy-1,4naphthoquinone with aryl iodides, which were prepared from 3,5-dimethylphenol, gave aryl-1,4-naphthoquinones. Treatment of the resulting aryl-1,4-naphthoquinones with aqueous ammonia, followed by oxidative cyclization and deprotection, successfully yielded phenanthroviridin aglycon (1,8-dihydroxy-3-methylbenzo[b]phenanthridine-7,12dione) and its analog (1,11-dihydroxy-3-methylbenzo[b] phenanthridine-7,12-dione).
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