Abstract
We report the total synthesis of jadomycins A, B, and l-digitoxosyl-phenanthroviridin. 2-Aryl-5-hydroxy-1,4-naphthoquinones, which were synthesized utilizing a Pd-catalyzed direct arylation of 5-hydroxy-1,4-naphthoquinone with aryl iodide, were converted into jadomycin A through introduction of l-isoleucine, followed by oxidative cyclization. Mitsunobu reaction of jadomycin A with 3,4-di-O-acetyl-l-digitoxose, which was prepared from commercially available 3,4-di-O-acetyl-6-deoxy-l-glucal, followed by deacetylation, gave jadomycin B. Additionally, the first total synthesis of l-digitoxosyl-phenanthroviridin was successful via Mitsunobu reaction of phenanthroviridin aglycon with 3,4-di-O-acetyl-l-digitoxose.
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