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Total Synthesis of (−)-Oridonin: An Interrupted Nazarov Approach

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posted on 11.12.2019, 16:06 by Lingran Kong, Fan Su, Hang Yu, Zhe Jiang, Yandong Lu, Tuoping Luo
An enantioselective total synthesis of (−)-oridonin is accomplished based on a key interrupted Nazarov reaction. The stereochemistry of the Nazarov/Hosomi–Sakurai cascade was first explored to forge a tetracyclic skeleton with challenging quaternary carbons. A delicate sequence of two ring-rearrangements and late-stage redox manipulations was carried out to achieve the de novo synthesis of this highly oxidized ent-kauranoid.