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
journal contributionposted on 18.09.2020 by Jing Zhang, Yehua Jin, Fayang G. Qiu
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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.