Jones Kerry E, Lara Fernando Martínez, Zavesky Blane P, Sarpong Richmond
Department of Chemistry, University of California, Berkeley, CA 94720, United States.
Discovery Chemistry, Small Molecule Discovery and Development, Crop Protection Discovery and Development, Corteva Agriscience, Indianapolis, IN 46268, United States.
Tetrahedron Lett. 2024 Mar 24;138. doi: 10.1016/j.tetlet.2024.154980. Epub 2024 Feb 24.
In this manuscript, an oxidative carbon-carbon bond forming reaction to construct the framework of alkaloids such as scholarinine A is explored using a constrained substrate. Instead of the desired carbon-carbon bond formation between an indole C3 position and a malonate group, a competing carbon-nitrogen bond between the malonate and indole C3 position was observed to form. This work adds to the growing body of substrates for oxidative carbon-carbon bond formation and importantly, demonstrates that these reactions are challenging for some conformationally constrained substrates.
在本论文中，使用一种受限底物探索了一种用于构建如马钱子碱A等生物碱骨架的氧化碳-碳键形成反应。未观察到在吲哚C3位与丙二酸酯基团之间形成预期的碳-碳键，而是观察到在丙二酸酯与吲哚C3位之间形成了竞争性的碳-氮键。这项工作增加了用于氧化碳-碳键形成的底物种类，并且重要的是，证明了这些反应对于一些构象受限的底物具有挑战性。
