Abstract
We report the total synthesis of jadomycins A, B, and L-digitoxosyl-phenanthroviridin. 2-Aryl-5-hydroxy1,4-naphthoquinones, which were synthesized utilizing a Pd-catalyzed direct arylation of 5-hydroxy-1,4naphthoquinone 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. (c) 2022 Elsevier Ltd. All rights reserved.
NSTL
Elsevier