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

Steven M. Allin, Joannah Towler, Sean N. Gaskell, Basu Saha, William P. Martin, Philip Bulman Page, Mark Edgar

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11 Citations (Scopus)


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.
Original languageEnglish
Pages (from-to)9538-9544
Number of pages7
Issue number49
Publication statusPublished - 10 Oct 2010

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