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Cleavage of a C–C bond is a diversifying process in the biogenesis of <i>seco</i>-terpenoids that has produced fascinating molecular structures. Leonuketal is an 8,9-<i>seco</i>-labdane terpenoid with a unique tetracyclic structure, owing to a C–C bond cleavage event in its biosynthesis. We report the first total synthesis of leonuketal, featuring an unusual Shapiro-type reaction as part of an enabling auxiliary ring strategy, and a novel Au-catalysed spirocyclization of a b-keto(enol)lactone.doi:10.26434/chemrxiv.12673757 fatcat:cedljetxuzdxva2kyxh2jybfaa