A Solid-Phase, Library Synthesis of Natural-Product-Like Derivatives from an Enantiomericaaly Pure Tetrahydroquinoline Scaffold

摘要

With the goal of developing a library synthesis of tetrahydroquinoline-derived natural-product-like small molecules, a practical synthesis of enantiomerically pure tetrahydroquinoline scaffold was achieved. An asymmetric aminohydroxylation reaction was the key step in this straegy. This scaffold was further immobilized onto the solid support for the library generation. The library was obtained from three diversity sites: (i) acylation of the hydroxyl group (R_1), (ii) coupling of the Fmoc-protectedamino acid to the amino group (R_2), and (iii) amidation of the N-terminal amine group (R_3).