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Updated: Jul 4, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Formal radical closure onto aromatic rings--a general route to carbocycles
Derrick L J Clive1, Rajesh Sunasee, Zhenhua Chen
1Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada. derrick.clive@ualberta.ca
Abstract:
A general method is described for indirectly effecting radical carbocyclization of an alkyl chain onto an aromatic ring. Birch reductive-alkylation of aromatic tert-butyl esters with alpha,omega-dibromides, chromium(vi)-mediated oxidation of the resulting 1,4-dienes and Finkelstein displacement of Br(-) with NaI gives cross-conjugated ketones that undergo radical cyclization. The products are easily aromatized to phenols by silylation, Saegusa oxidation and treatment with BiCl(3).H(2)O. A special feature of the route is that it allows attachment of a substituent to the original aromatic ring in place of the phenolic oxygen of the normal product.
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