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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Electrooxidative tricyclic 6-7-6 fused-system domino assembly to allocolchicines by a removable radical strategy
Yan Zhang1, Chanchan Ma1, Zhenzhi Cai1
1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, and Drug discovery & innovation center, College of Chemistry and Life Sciences, Zhejiang Normal University China zhangyan001@zjnu.edu.cn.
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.
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