Herein, we report the first stereoselective total synthesis of the eremophilane-type sesquiterpenoid (-)-peniroqueforin C using a chiral-pool strategy. This synthetic route features the use of readily available (S)-(+)-carvone as a chiral building block, Robinson annulation to construct the decalin system, substrate-controlled stereoselective methylation, single-step annulative construction of a tricyclic gamma-ylidene-butenolide with concomitant alkene transposition, and direct lactone-to-lactam conversion as key transformations.

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