Researchers Convert Isoxazoles to Pyrroles in 1-Pot O-to-C Skeletal Edit
Updated
Updated · Nature.com · Aug 19
Researchers Convert Isoxazoles to Pyrroles in 1-Pot O-to-C Skeletal Edit
2 articles · Updated · Nature.com · Aug 19
Summary
A new one-pot reaction replaces oxygen with carbon in isoxazoles, producing pyrroles that are often difficult to make through standard de novo syntheses.
The method hinges on an N-propargylic enaminone intermediate, giving chemists a retrosynthetic route orthogonal to traditional pyrrole-building strategies.
The team also found unexpected enaminone reactivity and built a computational model to predict which conformational features steer the reaction outcome.
Because isoxazoles and pyrroles differ by just 1 atom yet are both common in pharmaceutical and bioactive compounds, the work expands skeletal editing as a practical tool for accessing elusive heterocycle scaffolds.