Palladium-Catalyzed Arylative Dearomatization and Subsequent Aromatization/Dearomatization/Aza-Michael Addition: Access to Zephycarinatine and Zephygranditine Skeletons

We have developed a novel palladium-catalyzed arylative dearomatization and subsequent aromatization/dearomatization/aza-Michael addition process of Ugi adducts, enabling the rapid construction of diverse zephycarinatine and zephygranditine scaffolds containing two adjacent quaternary carbon stereocenters with excellent chemoselectivity and stereoselectivity in a rapid, step-economical, and highly efficient manner. This approach shows broad substrate scope and excellent functional-group tolerance with diverse electron-rich and electron-deficient aromatic substrates. The synthetic utility of this method is further demonstrated by versatile transformations of the products.

Automated summary

This novel palladium-catalyzed method allows for the rapid construction of diverse zephycarinatine and zephygranditine scaffolds with two adjacent quaternary carbon stereocenters in a rapid, step-economical, and highly efficient manner. It demonstrates broad substrate scope and excellent functional-group tolerance with various electron-rich and electron-deficient aromatic substrates, showing great synthetic utility through versatile transformations of the products.