research article

Solid-phase synthesis of natural product-like macrocycles by a sequence of Ugi-4CR and SNAr-based cycloetherification

Cristau, Pierre
•
Vors, Jean-Pierre
•
Zhu, Jieping  
2003
Tetrahedron Letters

An on-resin Ugi four-component reaction followed by an intramol. nucleophilic arom. substitution (SNAr) has been developed for the rapid access to biaryl-ether contg. macrocycles. Supported isocyanide was prepd. and used together with heptanal, butylamine, and 3-hydroxyphenylacetic acid for on-resin Ugi four-component reaction. [on SciFinder (R)]

Type
research article
DOI
10.1016/S0040-4039(03)01378-9
Author(s)
Cristau, Pierre
Vors, Jean-Pierre
Zhu, Jieping  
Date Issued

2003

Publisher

Elsevier

Published in
Tetrahedron Letters
Volume

44

Issue

30

Start page

5575

End page

5578

Subjects

Addition reaction (Ugi

•

four-component; solid-phase peptide synthesis of macrocycles from prepd. supported isocyanide by Ugi four-component reaction followed by nucleophilic arom. substitution-based cycloetherification); Substitution reaction (arom.; solid-phase peptide synthesis of macrocycles from prepd. supported isocyanide by Ugi four-component reaction followed by nucleophilic arom. substitution-based cycloetherification); Peptides Role: SPN (Synthetic preparation)

•

PREP (Preparation) (cyclic; solid-phase peptide synthesis of macrocycles from prepd. supported isocyanide by Ugi four-component reaction followed by nucleophilic arom. substitution-based cycloetherification); Etherification (cyclo; solid-phase peptide synthesis of macrocycles from prepd. supported isocyanide by Ugi four-component reaction followed by nucleophilic arom. substitution-based cycloetherification); Solid phase synthesis (peptide; solid-phase peptide synthesis of macrocycles from prepd. supported isocyanide by Ugi four-component reaction followed by nucleophilic arom. substitution-based cycloetherification); Cyclization (solid-phase peptide synthesis of macrocycles from prepd. supported isocyanide by Ugi four-component reaction followed by nucleophilic arom. substitution-based cycloetherification); Macrocyclic compounds Role: SPN (Synthetic preparation)

•

PREP (Preparation) (solid-phase peptide synthesis of macrocycles from prepd. supported isocyanide by Ugi four-component reaction followed by nucleophilic arom. substitution-based cycloetherification)

•

macrocycle biaryl ether contg solid phase peptide synthesis; isocyanide supported prepn Ugi reaction cycloetherification nucleophilic arom substitution

Note

CAN 139:277143

34-3

Amino Acids, Peptides, and Proteins

CNRS, Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.

Journal

written in English.

109-73-9 (Butylamine); 111-71-7 (Heptanal); 621-37-4 (3-Hydroxyphenylacetic acid); 389634-81-5; 604004-13-9D Role: RCT (Reactant), RACT (Reactant or reagent) (solid-phase peptide synthesis of macrocycles from prepd. supported isocyanide by Ugi four-component reaction followed by nucleophilic arom. substitution-based cycloetherification); 604004-11-7DP; 604004-12-8DP Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (solid-phase peptide synthesis of macrocycles from prepd. supported isocyanide by Ugi four-component reaction followed by nucleophilic arom. substitution-based cycloetherification); 604004-08-2P; 604004-09-3P; 604004-10-6P; 604004-12-8P; 604004-14-0P; 604004-15-1P; 604799-45-3P; 604799-74-8P; 604799-75-9P; 604799-76-0P Role: SPN (Synthetic preparation), PREP (Preparation) (solid-phase peptide synthesis of macrocycles from prepd. supported isocyanide by Ugi four-component reaction followed by nucleophilic arom. substitution-based cycloetherification)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58495