Infoscience

Journal article

SNAr-Based Macrocyclization: An Application to the Synthesis of Vancomycin Family Models

The first examples of macrocyclization using the intramol. SNAr reaction are reported. The method has allowed the efficient prepn. of the elusive 16-membered macrocyclic COD and DOE rings related to vancomycin. The mild conditions used allow the incorporation of very racemization-prone amino acids, such as p-methoxyphenylglycine, into the peptide chain. After serving as an activator, the nitro group ortho to the diaryl ether linkage is converted either into a chlorine or a hydrogen atom, thus achieving the substitution pattern found in the vancomycin family of glycopeptides. When compd. I 20 was submitted to the same macrocyclization conditions, two atropisomers II 21 and III 22 were isolated and characterized. [on SciFinder (R)]

    Keywords: Ring closure and formation (macrocyclization ; SNAr-based ; in synthesis of COD and DOE rings of vancomycin) ; SNAr macrocyclization COD DOE ring vancomycin

    Note:

    CAN 122:133774

    34-3

    Amino Acids, Peptides, and Proteins

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

    Journal

    0022-3263

    written in English.

    621-37-4 Role: RCT (Reactant), RACT (Reactant or reagent) (acylation by, of glycine fluoronitrophenylethylamide); 13269-15-3 (3-Hydroxybenzylamine hydrochloride) Role: RCT (Reactant), RACT (Reactant or reagent) (amidation by, of protected amino acids); 27460-85-1 Role: RCT (Reactant), RACT (Reactant or reagent) (amidation of, with (fluoronitro)penetylamine); 4530-20-5 (Boc-glycine) Role: RCT (Reactant), RACT (Reactant or reagent) (amidation of, with (fluoronitro)phenetylamine); 15761-38-3 Role: RCT (Reactant), RACT (Reactant or reagent) (amidation of, with hydroxybenzylamine); 160877-33-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and O-methylation of); 160877-40-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and coupling of, with amino acid hydroxybenzylamides); 157662-78-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and coupling of, with glycine deriv.); 160877-34-9P; 160877-45-2P; 160877-46-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and deamination of); 157662-75-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and diazotization-chlorination of); 160877-38-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis of); 157662-71-0P; 157662-72-1P; 160877-41-8P; 160877-42-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and macrocyclization of); 157662-73-2P; 157662-74-3P; 157662-77-6P; 157750-78-2P; 160877-43-0P; 160877-44-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of); 147949-76-6P; 160877-39-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and sequential deblocking and coupling of, with (fluoronitrophenyl)propionic acid); 157662-69-6P; 157662-70-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and sequential deblocking and coupling of, with hydroxyphenylacetic acid); 147949-74-4P; 147949-75-5P; 147949-89-1P; 157662-76-5P; 160877-35-0P; 160877-36-1P; 160877-37-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 1404-90-6P (Vancomycin) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of COD and DOE rings of, via SNAr-based macrocyclization); 15017-52-4 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with cyanide); 105-53-3 (Diethyl malonate) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with fluoronitrobenzyl bromide)

    Reference

    Record created on 2010-11-25, modified on 2016-08-08

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