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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Synthesis of Bispidine-Isoxazolidine-Fused Multicyclic Scaffolds via Nitrone [3+2] Cycloaddition: Toward
Georgy K Liklikadze1, Aleksei V Medved'ko1, Grigory S Simonyan1,2
1N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect, 47, Moscow119991, Russian Federation.
Abstract:
We present a highly efficient strategy for the assembly of bispidine-isoxazolidine-fused multicyclic structures via [3+2] cycloaddition of alkenes to a nitrone-functionalized bispidine framework. The reaction smoothly delivers diverse hybrid heterocycles featuring complex stereochemistry at the isoxazolidine-bispidine junction point in high yields and good selectivity. This approach opens a straightforward pathway to new synthetic analogues of natural compounds (primarily lupine alkaloids) and may prove to be useful for the discovery of new bioactive molecules and ligands for catalysis.
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