Synthesis of Deoxysugars through Manganese-promoted Redox Isomerization

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.

Name thesis:degree_name

Master

Department dc:contributor.department

Massachusetts Institute of Technology. Department of Chemistry

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2021

Author dc:creator

• Suh, Carolyn E.

Advisor dc:contributor.advisor

• Wendlandt, Alison

Statement dc:rights

• In Copyright - Educational Use Permitted
• Copyright MIT

Licence dc:rights.uri

• http://rightsstatements.org/page/InC-EDU/1.0/

Handle dc:identifier.uri

https://hdl.handle.net/1721.1/139107

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/139107