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)]
Cite this item
Beugelmans, R., Singh, G. P., Bois-Choussy, M., Chastanet, J., & Zhu, J. (1994). SNAr-Based Macrocyclization: An Application to the Synthesis of Vancomycin Family Models. The Journal of Organic Chemistry, 59(19), 5535–5542. https://doi.org/10.1021/jo00098a010
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1994
59
19
5535
42
CAN 122:133774
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
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)
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