Access to Fused Tricyclic γ-Butyrolactones, A Natural Product-like Scaffold.

Serendipitous findings of an acid mediated skeletal rearrangement of bicyclo-β-ketoester having cyclopropyl ring to access fused tricyclic γ-butyrolactones has been described. This novel transformation has been optimized to 30 mol% p-toluenesulfonic acid (p-TSA) in toluene using Dean-Stark apparatus, where the aldol condensation, cyclopropyl ring opening followed by cyclization took place in a single-pot operation. The resulting tricyclic compounds are interesting chemotype with natural product resemblance and may find useful applications in the future.