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

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 podoph...

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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
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container_issue 32
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container_title Organic & biomolecular chemistry
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creator Yuan, Peng
Liu, Rui
Zhu, Hui-Min
Liao, Zhixin
Xiang, Jia-Chen
Wu, An-Xin
description 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.
doi_str_mv 10.1039/d3ob00927k
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title An I-DMSO catalytic manifold enabled aromatization for C-ring editing of podophyllotoxone
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