Total synthesis of jadomycins A, B, and l-digitoxosyl-phenanthroviridin. (6th July 2022)

• Record Type: Journal Article
• Authors: Akagi, Yusuke; Mori, Yuta; Sato, Yudai; Iwasaki, Erika; Komatsu, Toshiya
• Is Part Of: Tetrahedron letters. Volume 101(2022)
• Publication Date: 2022-07-06
• Subjects: Digitoxose -- Jadomycin -- Mitsunobu reaction -- Palladium-catalyzed arylation -- Phenanthroviridin; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.153919
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: 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.