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

…, SN Gaskell, B Saha, WP Martin, PCB Page, M Edgar

Index: Allin, Steven M.; Towler, Joannah; Gaskell, Sean N.; Saha, Basu; Martin, William P.; Page, Philip C. Bulman; Edgar, Mark Tetrahedron, 2010 , vol. 66, # 49 p. 9538 - 9544

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Citation Number: 12

Abstract

Pyrroloisoquinoline-based peptidomimetics are of significant interest in bioorganic chemistry as these targets are known to exhibit type II′ β-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 ...