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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
Amide-Based Polyene Cyclization: Stereoselective Construction of cis- or trans-Octahydrobenzo[f]isoquinolines
Shi-Qi Cao1, Run-Ze Li1, Meng-Na Zhang2
1School of Pharmacy and State Key Laboratory of Natural Product Chemistry, Lanzhou University, Lanzhou 730000, China.
Abstract:
An amide-based polyene cyclization has been developed for the stereoselective synthesis of octahydrobenzo[f]isoquinolines. This reaction employs E-olefins as substrates and features a wide substrate scope, affording products in good yields with high diastereoselectivity. Notably, the stereochemical outcome is precisely controlled by the reaction temperature, representing a novel activation mode in polyene chemistry. Importantly, the synthesized octahydrobenzo[f]isoquinolines exhibit selective agonism for the δ-opioid receptor, providing valuable insights for developing more effective δ-opioid receptor agonists.
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