Home > Research > Publications & Outputs > Enolate amination and derivatization of a pyrro...

Research

Links

Text available via DOI:

View graph of relations

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

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Published

Standard

Enolate amination and derivatization of a pyrroloisoquinoline template: Towards novel peptidomimetics. / Allin, S.M.; Towler, J.; Gaskell, S.N. et al.
In: Tetrahedron, Vol. 66, No. 49, 04.12.2010, p. 9538-9544.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Allin, SM, Towler, J, Gaskell, SN, Saha, B, Martin, WP, Page, PCB & Edgar, M 2010, 'Enolate amination and derivatization of a pyrroloisoquinoline template: Towards novel peptidomimetics', Tetrahedron, vol. 66, no. 49, pp. 9538-9544. https://doi.org/10.1016/j.tet.2010.10.012

APA

Allin, S. M., Towler, J., Gaskell, S. N., Saha, B., Martin, W. P., Page, P. C. B., & Edgar, M. (2010). Enolate amination and derivatization of a pyrroloisoquinoline template: Towards novel peptidomimetics. Tetrahedron, 66(49), 9538-9544. https://doi.org/10.1016/j.tet.2010.10.012

Vancouver

Allin SM, Towler J, Gaskell SN, Saha B, Martin WP, Page PCB et al. Enolate amination and derivatization of a pyrroloisoquinoline template: Towards novel peptidomimetics. Tetrahedron. 2010 Dec 4;66(49):9538-9544. doi: 10.1016/j.tet.2010.10.012

Author

Allin, S.M. ; Towler, J. ; Gaskell, S.N. et al. / Enolate amination and derivatization of a pyrroloisoquinoline template : Towards novel peptidomimetics. In: Tetrahedron. 2010 ; Vol. 66, No. 49. pp. 9538-9544.

Bibtex

@article{b38b49f281ac4f478776fe4d6043f138,
title = "Enolate amination and derivatization of a pyrroloisoquinoline template: Towards novel peptidomimetics",
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.",
author = "S.M. Allin and J. Towler and S.N. Gaskell and B. Saha and W.P. Martin and P.C.B. Page and M. Edgar",
year = "2010",
month = dec,
day = "4",
doi = "10.1016/j.tet.2010.10.012",
language = "English",
volume = "66",
pages = "9538--9544",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "49",

}

RIS

TY - JOUR

T1 - Enolate amination and derivatization of a pyrroloisoquinoline template

T2 - Towards novel peptidomimetics

AU - Allin, S.M.

AU - Towler, J.

AU - Gaskell, S.N.

AU - Saha, B.

AU - Martin, W.P.

AU - Page, P.C.B.

AU - Edgar, M.

PY - 2010/12/4

Y1 - 2010/12/4

N2 - 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.

AB - 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.

U2 - 10.1016/j.tet.2010.10.012

DO - 10.1016/j.tet.2010.10.012

M3 - Journal article

VL - 66

SP - 9538

EP - 9544

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 49

ER -