Issue 28, 2021

Diversity-orientated synthesis of macrocyclic heterocycles using a double SNAr approach

Abstract

An efficient macrocyclisation approach based on the double aromatic nucleophilic substitution (SNACK) was developed. This methodology allows a facile incorporation of heterocyclic motifs into macrocyclic rings and rapid synthesis of a significant number of structurally diverse macrocycles. SNACK macrocyclisation enables preparation of stable diastereoisomers of conformationally restricted macrocycles (atropisomers). Practical application of SNACK macrocyclisation in a drug discovery project was exemplified by the identification of high affinity macrocyclic binders of B-cell lymphoma 6 (BCL6).

Graphical abstract: Diversity-orientated synthesis of macrocyclic heterocycles using a double SNAr approach

Supplementary files

Article information

Article type
Paper
Submitted
30 Mar 2021
Accepted
25 Jun 2021
First published
25 Jun 2021

Org. Biomol. Chem., 2021,19, 6274-6290

Diversity-orientated synthesis of macrocyclic heterocycles using a double SNAr approach

P. Raubo, R. J. Carbajo, W. McCoull, J. Raubo and M. Thomas, Org. Biomol. Chem., 2021, 19, 6274 DOI: 10.1039/D1OB00612F

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