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Total Synthesis of (±)-Leonuketal
preprintsubmitted on 20.07.2020, 03:49 and posted on 20.07.2020, 13:24 by Phillip Grant, Dan Furkert, Margaret Brimble
Cleavage 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.
Read the published paper
in Organic Letters