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Total Synthesis of Phenanthroviridin Aglycon and Its Analog
Author(s) -
Akagi Yusuke,
Harasawa Kohei,
Komatsu Toshiya
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100142
Subject(s) - chemistry , phenanthridine , aryl , naphthoquinone , aqueous solution , ammonia , oxidative phosphorylation , stereochemistry , medicinal chemistry , organic chemistry , alkyl , biochemistry
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).