The concise synthesis of a fungal metabolite, (+)-fusarochromanone (FC-101), was achieved via the oxidative sp(2) C-H bond olefination of an N-acetylaminochromanone with a chiral functionalized electron-rich alkene, catalyzed by an electron-deficient (eta(5)-cyclopentadienyl)rhodium(III) complex, [(CpRhCl2)-Rh-E](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.