Biomimetic Synthesis of Lavandiolides H, I, and K and Artematrolide F via Diels–Alder Reaction
Tian-Ze Li, Xiaotong Yang, Jinping Wang, Chang‐An Geng, Yun‐Bao Ma, Li‐Hua Su, Xue‐Mei Zhang, Ji‐Jun Chen
Abstract
The biomimetic synthesis of guaianolide dimers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the first time from naturally abundant arglabin in four to six steps with an overall yield up to 60%, and a series of natural product-like guaianolide dimers, trimer, and tetramer were also successfully synthesized. Notably, the trimeric compound exhibited antihepatoma cytotoxicity more potent than that of sorafenib with IC50 values of 6.2 μM (HepG2), 6.8 μM (Huh7), and 7.2 μM (SK-HEP-1).
Topics & Concepts
ChemistryTrimerTetramerMoietyYield (engineering)StereochemistryNatural productCytotoxicityCombinatorial chemistryDimerOrganic chemistryIn vitroBiochemistryMetallurgyEnzymeMaterials scienceMarine Sponges and Natural ProductsNatural product bioactivities and synthesisTraditional and Medicinal Uses of Annonaceae