A Solution- and Solid-Phase Approach to Tetrahydroquinoline-Derived Polycyclics Having a 10-Membered Ring

摘要

With the goal of library generation using a polycyclic derivative 5 having an enamide functional group,a simple and practical,enantioselective synthesis of tetrahydroquinoline derivative 2 was achieved.The phenolic hydroxyl group in compound 2 was utilized as an anchoring site for solid-phase synthesis.The ring closing metathesis approach yielded the desired polycyclic product 5 on solid phase in five steps (overall 40% yield).Compound 5 is a novel scaffold for the library generation of natural product-like polycyclics having a functionalized medium ring for obtaining a new class of small molecules to be utilized as chemical probes.