Synthesis of advanced Maillard products: 2-formylpyrrole alkaloids
•2-formylpyrroles are synthesized by an Achmatowicz oxidation and condensation reaction.•Access to differently substituted pyrroles through this sequence is available.•This reaction sequence is sensitive to steric bulk.•Bioactive natural products pyrrolezanthine and sinopyrine C are made using this...
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| Published in: | Results in Chemistry Vol. 4; p. 100526 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Elsevier B.V
01-01-2022
Elsevier |
| Subjects: | |
| Online Access: | Get full text |
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| Summary: | •2-formylpyrroles are synthesized by an Achmatowicz oxidation and condensation reaction.•Access to differently substituted pyrroles through this sequence is available.•This reaction sequence is sensitive to steric bulk.•Bioactive natural products pyrrolezanthine and sinopyrine C are made using this sequence.
A biologically-inspired method to access 2-formylpyrrole structures is reported using an Achmatowicz reaction and condensation sequence. This robust synthetic process has been used to access a variety of 2-formylpyrrole structures related to naturally isolated and bioactive compounds. Several families of pyrrole-based natural products have recently been isolated, and these structurally related compounds have been shown to demonstrate interesting bioactive properties. Synthesis targets include the natural products sinopyrine C and pyrrolezanthine. |
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| ISSN: | 2211-7156 2211-7156 |
| DOI: | 10.1016/j.rechem.2022.100526 |