An intramol. SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles I and II (R = NH2, NO2) related to F-O-G ring of teicoplanin. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted arom. rings were suitable for the macrocyclization reaction with tethered aryl oxides. The nonproteinogenic alpha -amino acid III, required for the synthesis of II, was prepd. via an asym. Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary. The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization. [on SciFinder (R)]
Title
A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction
Published in
Journal of Organic Chemistry
Volume
60
Issue
20
Pages
6389-96
Date
1995
ISSN
0022-3263
Note
CAN 123:228861
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
61036-62-2P (Teicoplanin) Role: PNU (Preparation, unclassified), PREP (Preparation) (a convergent synthesis of 14-membered ring analogs of the teicoplanin binding pocket via intramol. nucleophilic arom. substitution reactions); 99-10-5 (3,5-Dihydroxybenzoic acid); 331-25-9 (3-Fluorophenylacetic acid); 18942-49-9; 36394-75-9; 53088-68-9 (Methyl 3-chlorophenylacetate); 56613-80-0 ((R)-Phenylglycinol); 64123-77-9 (Methyl 3-fluorophenylacetate); 147949-76-6 Role: RCT (Reactant), RACT (Reactant or reagent) (a convergent synthesis of 14-membered ring analogs of the teicoplanin binding pocket via intramol. nucleophilic arom. substitution reactions); 2150-44-9P (Methyl 3,5-dihydroxybenzoate); 22908-28-7P; 22908-29-8P; 29640-98-0P; 29640-99-1P; 97522-06-0P; 163395-21-9P; 163395-22-0P; 163395-23-1P; 163395-24-2P; 163395-25-3P; 168292-12-4P; 168292-14-6P; 168292-15-7P; 168292-16-8P; 168292-17-9P; 168292-18-0P; 168292-20-4P; 168292-21-5P; 168292-22-6P; 169339-41-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (a convergent synthesis of 14-membered ring analogs of the teicoplanin binding pocket via intramol. nucleophilic arom. substitution reactions); 168292-11-3P; 168292-13-5P; 168292-19-1P Role: SPN (Synthetic preparation), PREP (Preparation) (a convergent synthesis of 14-membered ring analogs of the teicoplanin binding pocket via intramol. nucleophilic arom. substitution reactions)
Record creation date
2010-11-25
