Tetrahydroquinoline solid phase synthesis

Figure 15.26 Stereocontrolled solid-phase synthesis of tetrahydroquinoline-based natural-product-like polycyclics.

Arya, P. et al., Solution- and solid-phase synthesis of natural product-like tetrahydroquinoline-based... 

Derivatization of functional groups in a natural-product scaffold can also be effectively performed on the solid-phase. An example of this is the synthesis of a small compound collection (27-compounds) based on the tetrahydroquinoline scaffold. A chiral tetrahydroquinoline scaffold was synthesized in solution from 5-hydroxy-2-nitrobenzaldehyde (Scheme 4). The synthesis involved a key asymmetric aminohydroxylation step. This building block was anchored to the solid support with a Wang linker and diversity was introduced by selective deprotection and derivatization of the protected hydroxyl and amino substituents. 

Couve-Bonnaire, S. et al., A solid-phase, library synthesis of natural product-hke derivatives from an enantiomerically pure tetrahydroquinoline scaffold, J. Comb. Chem., 6, 73, 2004. 

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