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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...

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Autores principales: Zhang, Yan, Ma, Chanchan, Cai, Zhenzhi, Struwe, Julia, Chen, Shengjie, Xu, Jinming, Li, Shiyin, Zeng, Wangyu, Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
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.
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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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