Electrooxidative tricyclic 6–7–6 fused-system domino assembly to allocolchicines by a removable radical strategy. Issue 9 (20th April 2022)

• Record Type: Journal Article
• Authors: Zhang, Yan; Ma, Chanchan; Cai, Zhenzhi; Struwe, Julia; Chen, Shengjie; Xu, Jinming; Li, Shiyin; Zeng, Wangyu; Ackermann, Lutz
• Is Part Of: Green chemistry. Volume 24:Issue 9(2022)
• Page Start: 3697
• Page End: 3703
• Publication Date: 2022-04-20
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d2gc00684g
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : Natural allocolchicine and analogues derived thereof a tricyclic 6–7–6-system have been found as key scaffold of various biologically relevant molecules. Abstract : 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.