Total Synthesis of Phenanthroviridin Aglycon and Its Analog

We report the total synthesis of phenanthroviridin aglycon with interesting antibacterial and anticancer activities. A Pd-catalyzed direct arylation of 5-hydroxy-1,4-naphthoquinone 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-7,12-dione) and its analog (1,11-dihydroxy-3-methylbenzo[b]phenanthridine-7,12-dione).

Automated summary

The total synthesis of phenanthroviridin aglycon with interesting antibacterial and anticancer activities was reported in this study. The synthesis involved a Pd-catalyzed direct arylation of 5-hydroxy-1,4-naphthoquinone with aryl iodides prepared from 3,5-dimethylphenol, followed by treatment with aqueous ammonia, oxidative cyclization, and deprotection to yield the target compounds.