<i>Ortho</i>-Alkynylarylketones are versatile starting materials that have been reported to synthesize many valuable compounds in medicinal chemistry such as naphthofuran, indenone, and arylnaphthalenelactone core structures. To generate more effective method, we sought to develop the method to synthesize arylnaphthalenelactone by achieving one-pot synthesis, and cost-effective method by using inexpensive starting material, malonate ester, which enables to functionalize to a variety of structure. Furthermore, we also discover unexpected oxy-dearylation reaction which lead to the synthesis of furanonaphthol libraries. These approaches are applicable to create a wide variety of substrate scope which will be useful for other applications in organic synthesis. Moreover, the inhibitory activity of these classes of compounds on PTP1B enzyme was demonstrated with comparable activity to ursolic acid, a standard control.

One-pot silver-catalyzed and acid-mediated sequential reaction to access arylnaphthalenelactone and furanonaphthol libraries

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ACS Fall 2022

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