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Total Synthesis of Vinigrol


  • We thank the NIH-NIGMS (RO1 GM086584) for generous financial support of this program.


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Carbocyclic cage fight: The substrate-controlled total synthesis of vinigrol features a strategic oxidative dearomatization/Diels–Alder cycloaddition reaction and a subsequent palladium-catalyzed cyclization cascade to construct the carbocyclic core. The C4, C9, and C12 stereocenters were installed using either reduction or oxidation reactions, and the diterpenoid core was unraveled by a ring fragmentation reaction.

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