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

Autor:	Mark Edgar, Joannah M. R. Towler, William P. Martin, Steven M. Allin, Sean N. Gaskell, Philip C. Bulman Page, Basu Saha
Rok vydání:	2010
Předmět:	Template Chemistry Peptidomimetic Electrophilic amination Organic Chemistry Drug Discovery Electrophile Organic chemistry Bioorganic chemistry Stereoselectivity Biochemistry Chemical synthesis Amination
Zdroj:	Tetrahedron. 66:9538-9544
ISSN:	0040-4020
Popis:	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 aminating reagents based on azodicarboxylate functionality, and demonstrate the utility of our approach in the synthesis of a peptide target.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2b8c878deb89d35c0fc2cd95cfb2205c https://doi.org/10.1016/j.tet.2010.10.012 Zobrazit plný text záznamu Full Text from ScienceDirect