Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A
Feipeng Liu
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Department of Applied Chemistry, China Agricultural University, Beijing, 100193 China
Search for more papers by this authorZhe Dong
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Search for more papers by this authorCorresponding Author
Jianchun Wang
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Guangbin Dong
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Search for more papers by this authorFeipeng Liu
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Department of Applied Chemistry, China Agricultural University, Beijing, 100193 China
Search for more papers by this authorZhe Dong
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Search for more papers by this authorCorresponding Author
Jianchun Wang
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Search for more papers by this authorCorresponding Author
Prof. Dr. Guangbin Dong
Department of Chemistry, University of Chicago, Chicago, IL, 60637 USA
Search for more papers by this authorGraphical Abstract
A straightforward method for indenone synthesis was achieved by Pd/NBE-catalyzed annulation between simple aryl iodides and unsaturated carboxylic acid anhydrides. This method enabled streamlined syntheses of pauciflorol F and acredinone A.
Abstract
To show the synthetic utility of palladium/norbornene (Pd/NBE) cooperative catalysis, here we report concise syntheses of indenone-based natural products, pauciflorol F and acredinone A, which are enabled by direct annulation between aryl iodides and unsaturated carboxylic acid anhydrides. Compared to the previous indenone-preparation approaches, this method allows simple aryl iodides to be used as substrates with complete control of the regioselectivity. The total synthesis of acredinone A features two different Pd/NBE-catalyzed ortho acylation reactions for constructing penta-substituted arene cores, including the development of a new ortho acylation/ipso borylation.
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