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Issue 7, 2019

Synthesis of DNA-coupled isoquinolones and pyrrolidines by solid phase ytterbium- and silver-mediated imine chemistry

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Abstract

DNA-encoded libraries of chemically synthesized compounds are an important small molecule screening technology. The synthesis of encoded compounds in solution is currently restricted to a few DNA-compatible and water-tolerant reactions. Encoded compound synthesis of short DNA-barcodes covalently connected to solid supports benefits from a broad range of choices of organic solvents. Here, we show that this encoded chemistry approach allows for the synthesis of DNA-coupled isoquinolones by an Yb(III)-mediated Castagnoli–Cushman reaction under anhydrous reaction conditions and for the synthesis of highly substituted pyrrolidines by Ag(I)-mediated 1,3-dipolar azomethine ylide cycloaddition. An encoding scheme for these DNA-barcoded compounds based on a DNA hairpin is demonstrated.

Graphical abstract: Synthesis of DNA-coupled isoquinolones and pyrrolidines by solid phase ytterbium- and silver-mediated imine chemistry

Supplementary files

Article information


Submitted
25 Jan 2019
Accepted
21 Feb 2019
First published
26 Feb 2019

Med. Chem. Commun., 2019,10, 1082-1093
Article type
Research Article

Synthesis of DNA-coupled isoquinolones and pyrrolidines by solid phase ytterbium- and silver-mediated imine chemistry

M. Potowski, V. B. K. Kunig, F. Losch and A. Brunschweiger, Med. Chem. Commun., 2019, 10, 1082 DOI: 10.1039/C9MD00042A

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