Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

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

Access to Fused Tricyclic γ-Butyrolactones, A Natural Product-like Scaffold
Kishor L. Handore, D. Srinivasa Reddy, Hanuman P. Kalmode
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00794

DOI: 10.1021/acs.joc.7b00794

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