Stereoselective Diversity-Oriented Solution and Solid-Phase Synthesis of Tetrahydroquinoline-Based Polycyclic Derivatives

Abstract

A diversity-oriented solution and solid-phase synthesis of tetrahydroquinoline-based tricyclic derivatives has been achieved from enantiomerically pure, natural product-like bicyclic scaffold. The solution synthesis of enantiopure bicyclic scaffold was developed by asymmetric hetero Michael reaction. Our approach for the synthesis of polycyclic derivatives utilized regio-and stereoselective hetero Michael reaction and ringclosing metathesis as key steps in solution and on solid phase.

Tetrahydroquinoline-Derived Macrocyclic Toolbox: The Discovery of Antiangiogenesis Agents in Zebrafish Assay

“…As reported by us earlier, 28 we obtained an enantioenriched compound 2.2 from 2.1 in a number of wellestablished steps. One of the key advantages with this scaffold is that it can be accessed in several gms quantities in a short duration.…”

Advances in Solution- and Solid-Phase Synthesis toward the Generation of Natural Product-like Libraries

“…447 In several steps, compound 83.2 (Scheme 83) was obtained from 83.1 by a series of reactions. The carboxyl ester of compound 83.2 was then reduced to an alcohol and subjected to an amino group protection (N-alloc).…”

Metathesis Reactions in Solid‐Phase Organic Synthesis

“…They have prepared a wide variety of tetrahydroquinoline derivatives and polycyclic compounds including 6-, 8-, and 10-membered rings as shown in Figure 13.6. The phenolic hydroxyl group was utilized as an anchorage point to a Wang resin which can be conveniently cleaved with triflouroacetic acid (TFA) [33][34][35]. An extension of this work was published more recently in which an aminoindoline-based library was prepared.…”