Climbing the Oxidase Phase Ladder by Using Dioxygen as the Sole Oxidant: The Case Study of Costunolide
Kyriaki Gennaiou, Antonis Kelesidis, Alexandros L. Zografos
Abstract
Natural sesquiterpenoid lactones are prominent scaffolds in drug discovery. Despite the progress made in their synthesis, their extensive oxidative decoration makes their chemo- and stereoselective syntheses highly challenging. Herein, we report our effort to mimic part of the oxidase phase used in the costunolide pathway to achieve the protecting-group-free total synthesis of santamarine, dehydrocostus lactone, estafiatin, and nine more related natural sesquiterpenoid lactones by using dioxygen as the sole oxidant.
Topics & Concepts
ChemistryStereoselectivityOxidase testLactoneStereochemistryCombinatorial chemistryOxidative phosphorylationOrganic chemistryCatalysisBiochemistryEnzymeSesquiterpenes and Asteraceae StudiesNatural product bioactivities and synthesisPlant-derived Lignans Synthesis and Bioactivity