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

Allin, S.M. and Towler, J. and Gaskell, S.N. and Saha, B. and Martin, W.P. and Page, P.C.B. and Edgar, M. (2010) Enolate amination and derivatization of a pyrroloisoquinoline template : Towards novel peptidomimetics. Tetrahedron, 66 (49). pp. 9538-9544. ISSN 0040-4020

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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 aminating reagents based on azodicarboxylate functionality, and demonstrate the utility of our approach in the synthesis of a peptide target.

Item Type:
Journal Article
Journal or Publication Title:
Tetrahedron
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1300/1303
Subjects:
?? biochemistryorganic chemistrydrug discovery ??
ID Code:
202051
Deposited By:
Deposited On:
22 Aug 2023 13:50
Refereed?:
Yes
Published?:
Published
Last Modified:
16 Jul 2024 00:05