4.8 Article

Enantioselective Total Synthesis of (+)-Aberrarone

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Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c07150

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  1. ETH Zurich
  2. Swiss Chemical Industry

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This study presents the total synthesis of the complex molecule (+)-aberrarone using an Au-catalyzed-Sn-mediated cascade reaction, which efficiently closes four rings in the molecule. The method offers a stereoselective approach to synthesizing the natural product with a unique tetracyclic skeleton.
We disclose the first total synthesis of (+)-aberrarone, a diterpenoid natural product featuring a 5-5-5-6-fused tetracyclic skeleton. Key to the approach is a Au-catalyzed-Sn-mediated Meyer-Schuster-Nazarov-cyclopropanation-aldol cascade, which closes four rings in high yield. The convergent approach furnishes the natural product (+)-aberrarone stereoselectively in 15 steps. We highlight the benefits of using a Sn-alkoxide to considerably expand the opportunities of Au-catalysis for the synthesis of complex molecules.

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