An I-DMSO catalytic manifold enabled aromatization for C-ring editing of podophyllotoxone

• Published in: Organic & biomolecular chemistry 2023-08, Vol.21 (32), p.6468-6473
• Main Authors: Yuan, Peng, Liu, Rui, Zhu, Hui-Min, Liao, Zhixin, Xiang, Jia-Chen, Wu, An-Xin
• Format: Article
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d3ob00927k

The precise aromatization of the C-ring of podophyllotoxone to access value-added dehydropodophyllotoxin derivatives conventionally requires the use of equivalent amounts of unsustainable oxidants and suffers from inefficiencies. Taking advantage of the hydridic character of the C8 and C8′ of podophyllotoxone, we have developed an I 2 -DMSO catalytic manifold that enables a green and selective dehydrogenative aromatization to overcome these synthetic challenges. An unprecedented dehydrogenative amination of podophyllotoxone derivatives was also realized using aniline as the reaction partner. Effective dehydrogenative aromatization and dehydrogenative amination of podophyllotoxone derivatives have been realized using an I 2 -DMSO catalytic system.