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Tandem [5 + 2]/[4 + 2] Cycloadditions To Construct the [6–7–6] Tricyclic Skeleton of Icetexane Diterpenes: Total Synthesis of Euolutchuol E, Przewalskine E and Brussonol

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journal contribution
posted on 18.09.2020, 20:45 authored by Jing Zhang, Yehua Jin, Fayang G. Qiu
The collective total synthesis of the icetexane diterpenoids euolutchuol E, przewalskine E, and brussonol is described. An efficient synthetic strategy features two key transformations: (a) a tandem [5 + 2]/[4 + 2] cycloaddition reaction strategy to efficiently build the full-carbon skeleton of the icetexane diterpenoids; (b) an efficient aromatization of the C-ring of the icetexane diterpenoids using SeO2.