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

Thomas E. Nielsen; Sebastian Le Quement; Morten Meldal

doi:10.1016/j.tetlet.2005.09.080

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

Thomas E. Nielsen, Sebastian Le Quement, Morten Meldal^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › Research › peer-review

22 Citations (Scopus)

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%).

Original language	English
Journal	Tetrahedron Letters
Volume	46
Issue number	46
Pages (from-to)	7959-7962
Number of pages	4
ISSN	0040-4039
DOIs	https://doi.org/10.1016/j.tetlet.2005.09.080
Publication status	Published - 14 Nov 2005
Externally published	Yes

Keywords

Biaryl peptides
Scaffold synthesis
Solid phase reaction
Suzuki reaction

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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",

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doi = "10.1016/j.tetlet.2005.09.080",

language = "English",

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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

SN - 0040-4039

VL - 46

SP - 7959

EP - 7962

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

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

Abstract

Keywords

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