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Aromatic ent-pimaranes are a group of aromatized tricyclic diterpenoids that exhibit diverse bioactivities. In this work, the first total syntheses of two aromatic ent-pimaranes were achieved via a C-ABC construction sequence enabled by chiral auxiliary controlled asymmetric radical polyene cyclization, and the subsequent substrate-controlled stereo-/regio-specific hydroboration of alkene allowed for access to both natural products with C19 oxidation modifications.

Graphical abstract: Asymmetric syntheses of ent-pimarane diterpenoids

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