ETH Zürich, Department of Chemistry and Applied Biosciences, Laboratory of Organic Chemistry, Vladimir Prelog Weg 3, HCI H335, 8093 Zürich, Switzerland.
J Am Chem Soc. 2022 Aug 31;144(34):15475-15479. doi: 10.1021/jacs.2c07150. Epub 2022 Aug 19.
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.
我们首次全合成了（+）- aberrarone，这是一种具有 5-5-5-6 稠合四环骨架的二萜天然产物。该方法的关键是 Au 催化的 Sn 介导的 Meyer-Schuster-Nazarov 环丙烷化-缩合级联反应，该反应以高产率闭环。这种收敛方法以 15 步立体选择性地提供了天然产物（+）- aberrarone。我们强调了使用 Sn-醇盐来极大地扩展 Au 催化在复杂分子合成中的应用的好处。
