The first Rh-catalyzed enantioselective synthesis of a 3,4-polyfused oxindole ring system enabled by carboacylation of acrylic amides based on C−C activation is reported. This transformation provides a new entry to access 3,4-polyfused oxindoles bearing quaternary stereocenters. Trito pentacyclic 3,4-fused oxindoles were asymmetrically generated in good yields (up to 95%) with good to excellent enantioselectivity (88%−97% ee). Application in the first total synthesis of xylanigripones A was completed in 6 steps with a 14% overall yield.
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