Issue 64, 2017

Exploring sesquiterpene alkaloid-like scaffolds via Beckmann-transannular remodelling of beta-caryophyllene

Abstract

High-throughput screening (HTS) is the dominant approach to identify lead compounds in drug development. However, most compound-screening collections provide little structural or stereochemical complexity, which do not offer enough diversity to merit the modulation of many drug targets. Here we describe a facile strategy for the creation of diverse compounds with high structural and stereochemical complexity using readily available natural products, β-caryophyllene, as a synthetic starting point. Our findings demonstrate that a cascaded Beckmann-transannular protocol transforms macrocyclic natural products into poly-heterocyclic unnatural skeletal types. These compounds are significantly more complex and diverse than those in standard screening collections.

Graphical abstract: Exploring sesquiterpene alkaloid-like scaffolds via Beckmann-transannular remodelling of beta-caryophyllene

Supplementary files

Article information

Article type
Paper
Submitted
25 Jul 2017
Accepted
13 Aug 2017
First published
18 Aug 2017
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2017,7, 40510-40516

Exploring sesquiterpene alkaloid-like scaffolds via Beckmann-transannular remodelling of beta-caryophyllene

S. Ma, J. Yu, H. Fan, Z. Li, A. Zhang and Q. Zhang, RSC Adv., 2017, 7, 40510 DOI: 10.1039/C7RA08196K

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