Concise synthesis of fungal metabolite (+)-fusarochromanone via rhodium(III)-catalyzed oxidative sp2 C-H bond olefination

Abstract

The concise synthesis of a fungal metabolite, (+)-fusarochromanone (FC-101), was achieved via the oxidative sp2 C-H bond olefination of an N-acetylaminochromanone with a chiral functionalized electron-rich alkene, catalyzed by an electron-deficient (η5-cyclopentadienyl)rhodium(III) complex, [CpERhCl2]2, under ambient conditions as the key step. This protocol was applied to various acetanilides and functionalized electron-rich alkenes for the syntheses of fusarochromanone analogs.