Issue 71, 2020

First total synthesis of versicotide A, B and C

Abstract

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.

Graphical abstract: First total synthesis of versicotide A, B and C

Supplementary files

Article information

Article type
Paper
Submitted
12 nov 2020
Accepted
24 nov 2020
First published
09 dec 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 43653-43659

First total synthesis of versicotide A, B and C

L. Posada, D. Davyt and G. Serra, RSC Adv., 2020, 10, 43653 DOI: 10.1039/D0RA09635K

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