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First total synthesis of versicotide A, B and C

The syntheses of versicotides A–C, natural products containing anthranilic acid and NMe-Ala, were achieved by solid phase peptide synthesis on 2-chlorotrityl resin followed by solution phase macrocyclization. Using an oxyma additive, the difficult coupling reactions to the deactivated aromatic amine...

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Detalles Bibliográficos
Autores principales: Posada, Laura, Davyt, Danilo, Serra, Gloria
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9058379/
https://www.ncbi.nlm.nih.gov/pubmed/35519702
http://dx.doi.org/10.1039/d0ra09635k
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author Posada, Laura
Davyt, Danilo
Serra, Gloria
author_facet Posada, Laura
Davyt, Danilo
Serra, Gloria
author_sort Posada, Laura
collection PubMed
description The syntheses of versicotides A–C, natural products containing anthranilic acid and NMe-Ala, were achieved by solid phase peptide synthesis on 2-chlorotrityl resin followed by solution phase macrocyclization. Using an oxyma additive, the difficult coupling reactions to the deactivated aromatic amine of o-aminobenzoic acid, were performed in high yield, avoiding anthranilic rearrangements or side reactions.
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spelling pubmed-90583792022-05-04 First total synthesis of versicotide A, B and C Posada, Laura Davyt, Danilo Serra, Gloria RSC Adv Chemistry The syntheses of versicotides A–C, natural products containing anthranilic acid and NMe-Ala, were achieved by solid phase peptide synthesis on 2-chlorotrityl resin followed by solution phase macrocyclization. Using an oxyma additive, the difficult coupling reactions to the deactivated aromatic amine of o-aminobenzoic acid, were performed in high yield, avoiding anthranilic rearrangements or side reactions. The Royal Society of Chemistry 2020-12-09 /pmc/articles/PMC9058379/ /pubmed/35519702 http://dx.doi.org/10.1039/d0ra09635k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Posada, Laura
Davyt, Danilo
Serra, Gloria
First total synthesis of versicotide A, B and C
title First total synthesis of versicotide A, B and C
title_full First total synthesis of versicotide A, B and C
title_fullStr First total synthesis of versicotide A, B and C
title_full_unstemmed First total synthesis of versicotide A, B and C
title_short First total synthesis of versicotide A, B and C
title_sort first total synthesis of versicotide a, b and c
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9058379/
https://www.ncbi.nlm.nih.gov/pubmed/35519702
http://dx.doi.org/10.1039/d0ra09635k
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