Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization
Name
suh-carolsuh-ms-chemistry-2021-thesis.pdf
Description
Thesis PDF
Size
3.49 MB
Format
Adobe PDF
Checksum (MD5)
1fbe5fcf101e8ac34eeb1e12ebe3aed1
Author(s)
Suh, Carolyn E.
Advisor(s)
Wendlandt, Alison
Date Issued
June 2021
Publisher
Massachusetts Institute of Technology
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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