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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements