Uchiyama Ami, Ohta Hikari, Ogawa Yuya, Sasaki Ikuo, Sugimura Hideyuki
Department of Chemistry and Bioscience, Faculty of Science and Technology, Aoyama Gakuin University, 5-10-1, Fuchinobe, Chuo-ku, Sagamihara 252-5258, Japan.
J Org Chem. 2024 Sep 6;89(17):12864-12870. doi: 10.1021/acs.joc.4c01608. Epub 2024 Aug 20.
The synthesis of a spirolactone analogue of xylapyrraside B, a potent antioxidant agent, is described. The key step is the stereoselective formation of the spirolactone skeleton via the formal [3+2] annulation of the isopropylidene-protected glyceraldehyde and δ-methylene lactone, mediated by trifluoroborane etherate. This study addresses the stereoselective synthesis of pyrrolomorpholine spiroketal alkaloids, enabling the production of these bioactive compounds and their analogues.
本文描述了一种强效抗氧化剂木拉吡甙B的螺内酯类似物的合成。关键步骤是通过三氟化硼乙醚介导的异亚丙基保护的甘油醛与δ-亚甲基内酯的形式上的[3+2]环化反应，立体选择性地形成螺内酯骨架。这项研究解决了吡咯吗啉螺缩酮生物碱的立体选择性合成问题，能够生产这些生物活性化合物及其类似物。
