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of a C–C bond is a diversifying process in the biogenesis of seco-terpenoids
that has produced fascinating molecular structures. Leonuketal is an 8,9-seco-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.