An efficient chloro-deamination procedure was developed and a remarkable deuterium isotope effect indicating a radical mechanism was documented. Key to success was the coexistence of a reductant (CuCl) and a ligand-transfer agent (CuCl2) in the reaction medium employing CD3CN as co-solvent of CCl4. The procedure was applied to the synthesis of advanced vancomycin models. [on SciFinder (R)]
Title
An efficient chloro-deamination procedure, application to the synthesis of advanced vancomycin C-O-D-O-E ring
Published in
Synlett
Issue
10
Pages
1159-1161
Date
1998
ISSN
0936-5214
Note
CAN 130:25333
34-3
Amino Acids, Peptides, and Proteins
Institut Chimie Substances Naturelles,Gif-sur-Yvette,Fr.
Journal
written in English.
1404-90-6P (Vancomycin) Role: PNU (Preparation, unclassified), PREP (Preparation) (synthesis of advanced vancomycin C-O-D-O-E ring via chloro-deamination); 216318-64-8; 216318-65-9; 216318-71-7 Role: RCT (Reactant), RACT (Reactant or reagent) (synthesis of advanced vancomycin C-O-D-O-E ring via chloro-deamination); 216318-66-0P; 216318-67-1P; 216318-76-2P; 216318-85-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (synthesis of advanced vancomycin C-O-D-O-E ring via chloro-deamination); 216220-79-0P; 216318-68-2P; 216318-69-3P; 216318-72-8P Role: SPN (Synthetic preparation), PREP (Preparation) (synthesis of advanced vancomycin C-O-D-O-E ring via chloro-deamination)
Record creation date
2010-11-25
