Sequential Cu(II)-Catalyzed Multicomponent C-N Coupling, Nucleophilic Addition, and Cyclization Cascade: A Diastereoselective Approach to Carboxamide-Embedded Hexahydrobenzofuran Core.

Cascade or domino reactions serve as a powerful technique for the synthesis of complex organic scaffolds in one pot. Herein, a Cu(II)-catalyzed and silica gel-assisted multicomponent reaction (MCR) between bromoalkyne-tethered cyclohexadienones, amides, and water for the construction of hexahydrobenzofuran-3-carboxamide is developed. The reaction proceeds via a C-N coupling reaction followed by hydrative cyclization of ynamide intermediates. Notably, good to excellent diastereoselectivity is complementary of this reaction.

Gold-catalyzed homo- and cross-annulation of alkynyl carboxylic acids: a facile access to substituted 4-hydroxy 2H-pyrones and total synthesis of pseudopyronine A.

A Au(i)-catalyzed homo- and cross-annulation reaction of alkynyl carboxylic acids offering 3,6-disubstituted 4-hydroxy 2H-pyrones has been demonstrated. The reaction tolerates various substituted alkynyl carboxylic acids and moderate to good yields of α-pyrone scaffolds have been observed. Later, a gram-scale reaction of the acid and the total synthesis of the natural product pseudopyronine A have been carried out successfully.