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Electrooxidative tricyclic 6–7–6 fused-system domino assembly to allocolchicines by a removable radical strategy
Natural allocolchicine and analogues derived thereof a tricyclic 6–7–6-system have been found as key scaffold of various biologically relevant molecules. However, the direct preparation of the allocolchicine motif remains difficult to date. Herein, we report on an electrooxidative radical cyclizatio...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9086860/ https://www.ncbi.nlm.nih.gov/pubmed/35694222 http://dx.doi.org/10.1039/d2gc00684g |
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author | Zhang, Yan Ma, Chanchan Cai, Zhenzhi Struwe, Julia Chen, Shengjie Xu, Jinming Li, Shiyin Zeng, Wangyu Ackermann, Lutz |
author_facet | Zhang, Yan Ma, Chanchan Cai, Zhenzhi Struwe, Julia Chen, Shengjie Xu, Jinming Li, Shiyin Zeng, Wangyu Ackermann, Lutz |
author_sort | Zhang, Yan |
collection | PubMed |
description | Natural allocolchicine and analogues derived thereof a tricyclic 6–7–6-system have been found as key scaffold of various biologically relevant molecules. However, the direct preparation of the allocolchicine motif remains difficult to date. Herein, we report on an electrooxidative radical cyclization of biarylynones with various carbon- and heteroatom-centered radical precursors via a sequential radical addition/7-endo-trig/radical cyclization domino reaction. This approach provides a step-economical and strategically novel disconnection for the facile assembly of a wide range of carbocyclic 6–7–6 fused ring systems. Remarkably, the sulfonyl group on the products could be easily removed by photocatalysis at room temperature with high yields. |
format | Online Article Text |
id | pubmed-9086860 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90868602022-06-08 Electrooxidative tricyclic 6–7–6 fused-system domino assembly to allocolchicines by a removable radical strategy Zhang, Yan Ma, Chanchan Cai, Zhenzhi Struwe, Julia Chen, Shengjie Xu, Jinming Li, Shiyin Zeng, Wangyu Ackermann, Lutz Green Chem Chemistry Natural allocolchicine and analogues derived thereof a tricyclic 6–7–6-system have been found as key scaffold of various biologically relevant molecules. However, the direct preparation of the allocolchicine motif remains difficult to date. Herein, we report on an electrooxidative radical cyclization of biarylynones with various carbon- and heteroatom-centered radical precursors via a sequential radical addition/7-endo-trig/radical cyclization domino reaction. This approach provides a step-economical and strategically novel disconnection for the facile assembly of a wide range of carbocyclic 6–7–6 fused ring systems. Remarkably, the sulfonyl group on the products could be easily removed by photocatalysis at room temperature with high yields. The Royal Society of Chemistry 2022-04-13 /pmc/articles/PMC9086860/ /pubmed/35694222 http://dx.doi.org/10.1039/d2gc00684g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Zhang, Yan Ma, Chanchan Cai, Zhenzhi Struwe, Julia Chen, Shengjie Xu, Jinming Li, Shiyin Zeng, Wangyu Ackermann, Lutz Electrooxidative tricyclic 6–7–6 fused-system domino assembly to allocolchicines by a removable radical strategy |
title | Electrooxidative tricyclic 6–7–6 fused-system domino assembly to allocolchicines by a removable radical strategy |
title_full | Electrooxidative tricyclic 6–7–6 fused-system domino assembly to allocolchicines by a removable radical strategy |
title_fullStr | Electrooxidative tricyclic 6–7–6 fused-system domino assembly to allocolchicines by a removable radical strategy |
title_full_unstemmed | Electrooxidative tricyclic 6–7–6 fused-system domino assembly to allocolchicines by a removable radical strategy |
title_short | Electrooxidative tricyclic 6–7–6 fused-system domino assembly to allocolchicines by a removable radical strategy |
title_sort | electrooxidative tricyclic 6–7–6 fused-system domino assembly to allocolchicines by a removable radical strategy |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9086860/ https://www.ncbi.nlm.nih.gov/pubmed/35694222 http://dx.doi.org/10.1039/d2gc00684g |
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