Total syntheses of dihydro-β-agarofuran natural products.

Abstract

Dihydro-β-agarofuran (DHβAF) sesquiterpenoids constitute a large family of natural products characterized by a tricyclic architecture comprising trans-decalin and tetrahydrofuran rings, and oxygen functionalities on them. Their pharmacologically and agriculturally important biological properties and intriguing molecular architectures have attracted considerable attention from synthetic organic and medicinal chemists. In 2020, our group achieved a scalable total synthesis of this type of natural product, (-)-isocelorbicol, by developing a highly stereocontrolled protocol, which enabled elaboration to naturally occurring ester derivatives, celafolins B-1, B-2, and B-3. Afterward, the total syntheses of more complex DHβAF sesquiterpenoids, (-)-euonyminol and (-)-euonymine, were reported by 2 research groups via current state-of-the-art methods. This review summarizes the total syntheses of DHβAF natural products from 1979 to 2021.