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Issue 64, 2017
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Exploring sesquiterpene alkaloid-like scaffolds via Beckmann-transannular remodelling of beta-caryophyllene

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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

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Publication details

The article was received on 25 Jul 2017, accepted on 13 Aug 2017 and first published on 18 Aug 2017


Article type: Paper
DOI: 10.1039/C7RA08196K
RSC Adv., 2017,7, 40510-40516
  • Open access: Creative Commons BY-NC license
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    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

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