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

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)]


Published in:
Tetrahedron Letters, 44, 30, 5575-5578
Year:
2003
Keywords:
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
0040-4039
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)
Laboratories:




 Record created 2010-11-25, last modified 2018-09-13


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