Several families of pyrrole-based natural products have recently been isolated and shown to possess interesting anti-inflammatory properties. These families of compounds share a similarity in structure. All of these compounds are derived from similar biological pathways which involve the combination of sugar metabolites and amines. Making use of a biomimetic approach, a concise and high-yielding synthesis of the pyrrole core of this family of natural products has been developed and used to produce a library of related compounds.<br/><br/>The members of the library are accessed through an Achmatowicz oxidation of a furfuryl alcohol to give a synthetic analog of the biosynthetic precursor. The product of this reaction can condense with amines to give the pyrrole core directly. A broad scope of pyrroles have been accessed using this method.

Heterocycle libraries based on natural anti-imflammatories

2019 Spring National Meeting

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