Fan Zhoulong, Cai Xinpei, Sheng Tao, Yu Jin-Quan
Department of Chemistry, The Scripps Research Institute 10550 North Torrey Pines Road La Jolla CA 92037 USA
Chem Sci. 2025 Apr 29. doi: 10.1039/d5sc00711a.
Bicyclo[3.2.0]heptane lactones represent an important scaffold in bioactive molecules. Herein, we report a diastereoselective synthetic disconnection to access bicyclo[3.2.0]heptane lactones from bicyclo[1.1.1]pentane carboxylic acids, which proceeds through palladium-catalyzed C-H activation and C-C cleavage processes. By using two different classes of ligands, MPAA and pyridone-amine, either all- arylated bicyclo[3.2.0]heptane lactones or non-arylated ones can be synthesized. The bicyclo[3.2.0]heptane lactone products were converted into multiple substituted cyclobutane, γ-lactone, and oxobicyclo[3.2.0]heptane derivatives to showcase the synthetic versatility of this method.
双环[3.2.0]庚烷内酯是生物活性分子中的一种重要骨架。在此，我们报道了一种从双环[1.1.1]戊烷羧酸出发，通过钯催化的C-H活化和C-C裂解过程实现双环[3.2.0]庚烷内酯的非对映选择性合成切断方法。通过使用两类不同的配体，即MPAA和吡啶酮-胺，可以合成全芳基化的双环[3.2.0]庚烷内酯或非芳基化的双环[3.2.0]庚烷内酯。双环[3.2.0]庚烷内酯产物被转化为多种取代的环丁烷、γ-内酯和氧杂双环[3.2.0]庚烷衍生物，以展示该方法的合成通用性。
