Enolate amination and derivatization of a pyrroloisoquinoline template: towards novel peptidomimetics

Allin, Steven M., Towler, Joannah, Gaskell, Sean N., Saha, Basu, Martin, William P., Bulman Page, Philip and Edgar, Mark (2010) Enolate amination and derivatization of a pyrroloisoquinoline template: towards novel peptidomimetics. Tetrahedron, 66 (49). pp. 9538-9544.

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Abstract

Pyrroloisoquinoline-based peptidomimetics are of significant interest in bioorganic chemistry as these targets are known to exhibit type II' ß-turn activity. In this paper we present a novel approach to such pyrroloisoquinoline templates based on a stereoselective N-acyliminium-mediated cyclization reaction to construct the heterocyclic core, coupled with an enolate amination protocol. We have applied both symmetrical and unsymmetrical electrophilic aminating reagents based on azodicarboxylate functionality, and demonstrate the utility of our approach in the synthesis of a peptide target.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	Rachel Smith
Date Deposited:	22 Mar 2011 12:01
Last Modified:	22 Dec 2022 13:30
URI:	https://ueaeprints.uea.ac.uk/id/eprint/26852
DOI:	10.1016/j.tet.2010.10.012

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