Total Synthesis of (+)-Polyoxamic Acid via Visible-Light-Mediated Photocatalytic β-Scission and 1,5-Hydrogen Atom Transfer of Glucose Derivative
Takuro Matsuoka, Shinsuke Inuki, Takashi Miyagawa, Shinya Oishi, Hiroaki Ohno
Abstract
A total synthesis of polyoxamic acid has been achieved. The key feature of the synthetic route is a visible-light-mediated β-scission and carbon-to-carbon 1,5-hydrogen atom transfer (1,5-HAT) to provide the functionalized alditol under mild conditions. This type of carbon-to-carbon 1,5-HAT initiated by C(sp3)-centered radicals has been scarcely reported. Furthermore, the reaction was adapted for flow chemistry, facilitating the total synthesis of polyoxamic acid.
Topics & Concepts
ChemistryHydrogen atomPhotocatalysisPhotochemistryRadicalCarbon fibersCarbon atomHydrogenDerivative (finance)Bond cleavageVisible spectrumElectron transferCatalysisOrganic chemistryEconomicsFinancial economicsComposite numberComposite materialPhysicsMaterials scienceOptoelectronicsAlkylRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsSulfur-Based Synthesis Techniques