Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet-Spengler reactions

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Standard

Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet-Spengler reactions. / Nielsen, Thomas E.; Le Quement, Sebastian; Meldal, Morten.

I: Tetrahedron Letters, Bind 46, Nr. 46, 14.11.2005, s. 7959-7962.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Nielsen, TE, Le Quement, S & Meldal, M 2005, 'Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet-Spengler reactions', Tetrahedron Letters, bind 46, nr. 46, s. 7959-7962. https://doi.org/10.1016/j.tetlet.2005.09.080

APA

Nielsen, T. E., Le Quement, S., & Meldal, M. (2005). Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet-Spengler reactions. Tetrahedron Letters, 46(46), 7959-7962. https://doi.org/10.1016/j.tetlet.2005.09.080

Vancouver

Nielsen TE, Le Quement S, Meldal M. Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet-Spengler reactions. Tetrahedron Letters. 2005 nov. 14;46(46):7959-7962. https://doi.org/10.1016/j.tetlet.2005.09.080

Author

Nielsen, Thomas E. ; Le Quement, Sebastian ; Meldal, Morten. / Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet-Spengler reactions. I: Tetrahedron Letters. 2005 ; Bind 46, Nr. 46. s. 7959-7962.

Bibtex

@article{2111f8d05d7b40afa29a96983283ec4d,
title = "Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet-Spengler reactions",
abstract = "Solid-supported masked peptide aldehydes containing 3- or 4-iodophenylalanine residues were subjected to Pd-catalyzed Suzuki cross-coupling reactions with arylboronic acids. The biarylalanines generated were applied in intramolecular N-acyliminium Pictet-Spengler reactions. In this way, a range of pharmacologically interesting aryl-substituted pyrroloisoquinolines was obtained in excellent purity (>95%).",
keywords = "Biaryl peptides, Scaffold synthesis, Solid phase reaction, Suzuki reaction",
author = "Nielsen, {Thomas E.} and {Le Quement}, Sebastian and Morten Meldal",
note = "Funding Information: The Danish National Research Foundation is gratefully acknowledged for financial support. ",
year = "2005",
month = nov,
day = "14",
doi = "10.1016/j.tetlet.2005.09.080",
language = "English",
volume = "46",
pages = "7959--7962",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Pergamon Press",
number = "46",

}

RIS

TY - JOUR

T1 - Solid-phase synthesis of biarylalanines via Suzuki cross-coupling and intramolecular N-acyliminium Pictet-Spengler reactions

AU - Nielsen, Thomas E.

AU - Le Quement, Sebastian

AU - Meldal, Morten

N1 - Funding Information: The Danish National Research Foundation is gratefully acknowledged for financial support.

PY - 2005/11/14

Y1 - 2005/11/14

N2 - Solid-supported masked peptide aldehydes containing 3- or 4-iodophenylalanine residues were subjected to Pd-catalyzed Suzuki cross-coupling reactions with arylboronic acids. The biarylalanines generated were applied in intramolecular N-acyliminium Pictet-Spengler reactions. In this way, a range of pharmacologically interesting aryl-substituted pyrroloisoquinolines was obtained in excellent purity (>95%).

AB - Solid-supported masked peptide aldehydes containing 3- or 4-iodophenylalanine residues were subjected to Pd-catalyzed Suzuki cross-coupling reactions with arylboronic acids. The biarylalanines generated were applied in intramolecular N-acyliminium Pictet-Spengler reactions. In this way, a range of pharmacologically interesting aryl-substituted pyrroloisoquinolines was obtained in excellent purity (>95%).

KW - Biaryl peptides

KW - Scaffold synthesis

KW - Solid phase reaction

KW - Suzuki reaction

UR - http://www.scopus.com/inward/record.url?scp=26844451459&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2005.09.080

DO - 10.1016/j.tetlet.2005.09.080

M3 - Journal article

AN - SCOPUS:26844451459

VL - 46

SP - 7959

EP - 7962

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 46

ER -

ID: 326846788