Total Synthesis of (+)-Polyoxamic Acid via Visible-Light-Mediated Photocatalytic β-Scission and 1,5-Hydrogen Atom Transfer of Glucose Derivative
- 19 May 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (12), 8271-8278
- https://doi.org/10.1021/acs.joc.0c00910
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 also adapted for flow chemistry, facilitating the total synthesis of polyoxamic acid.Keywords
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