Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization
Author(s)
Suh, Carolyn E.
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Advisor
Wendlandt, Alison
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Deoxysugars feature prominently in many bioactive natural products and pharmaceutical compounds. Many synthetic routes towards deoxysugars rely on protecting groups to achieve selective outcomes. Here we report a concise synthetic strategy to access a diverse set of 2- and 4-deoxysugars using a Mn-promoted redox isomerization step that avoids lengthy protecting group manipulations. We determine the resting state of the manganese catalyst to be Mn(II). We demonstrate subsequent derivatizations with the ketone moiety to access branched sugars and amino sugars as well, showcasing the versatility and utility of this method.
Date issued
2021-06Department
Massachusetts Institute of Technology. Department of ChemistryPublisher
Massachusetts Institute of Technology