Efficient synthesis of dihydronaphthalenes cerium-catalyzed annulation of 1-alkoxy substituted 1-isochromenes with cinnamic acids.

Org Biomol Chem

Key Laboratory of Evolution & Marine Biodiversity (Ministry of Education) and Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, China.

Published: January 2025

Dihydronaphthalenes play a crucial role in bioactive natural products and new drug discovery, and efficient and economic strategies to build them are needed. Herein, we disclose a highly efficient method to prepare dihydronaphthalenes a cerium-catalyzed cycloaddition of 1-isochromenes with cinnamic acids. This newly developed method not only features a broad and low-cost substrate scope and mild conditions but also exhibits very high functional group tolerance, including hydroxyl, borate ester and ester group substituents. In addition, the practicality of this general strategy is demonstrated by gram-scale reactions and derivatizations, and all of the reactions proceed smoothly to afford the desired compounds in excellent yields.

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http://dx.doi.org/10.1039/d4ob01895hDOI Listing

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Efficient synthesis of dihydronaphthalenes cerium-catalyzed annulation of 1-alkoxy substituted 1-isochromenes with cinnamic acids.

Org Biomol Chem

January 2025

Key Laboratory of Evolution & Marine Biodiversity (Ministry of Education) and Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, China.

Dihydronaphthalenes play a crucial role in bioactive natural products and new drug discovery, and efficient and economic strategies to build them are needed. Herein, we disclose a highly efficient method to prepare dihydronaphthalenes a cerium-catalyzed cycloaddition of 1-isochromenes with cinnamic acids. This newly developed method not only features a broad and low-cost substrate scope and mild conditions but also exhibits very high functional group tolerance, including hydroxyl, borate ester and ester group substituents.

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