Issue 3, 2024, Issue in Progress

Total synthesis of (±)-auranthine confirmed its refined structure

Abstract

Auranthine, isolated in 1986 from Penicillium aurantiogriseum, is a fungal benzodiazepine. Through the successful total synthesis of (±)-auranthine, we confirmed the refined structure of natural (−)-auranthine. We established that natural (−)-auranthine is a fused quinazolino benzodiazepine dione 1 featuring an acyclic aliphatic nitrile moiety, thereby disproving the proposed structure 2.

Graphical abstract: Total synthesis of (±)-auranthine confirmed its refined structure

Supplementary files

Article information

Article type
Paper
Submitted
02 Nov 2023
Accepted
23 Dec 2023
First published
04 Jan 2024
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2024,14, 1649-1654

Total synthesis of (±)-auranthine confirmed its refined structure

M. Reinker, S. A. Kalinina and D. V. Kalinin, RSC Adv., 2024, 14, 1649 DOI: 10.1039/D3RA07483H

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