Organic letters

Formation of benzo-fused carbocycles by formal radical cyclization onto an aromatic ring

DLJ Clive, R Sunasee

Index: Clive, Derrick L. J.; Sunasee, Rajesh Organic Letters, 2007 , vol. 9, # 14 p. 2677 - 2680

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Citation Number: 28

Abstract

An indirect method for effecting radical carbocyclization onto aromatic rings is described. Cross-conjugated dienones such as 13, readily prepared by Birch reduction of aromatic tert- butyl esters, in situ alkylation, and oxidation (10→ 11→ 12→ 13), undergo radical cyclization; the products (14) are aromatized by silylation, Saegusa oxidation, and treatment with BiCl3⊙ H2O. A noteworthy feature of this route is that it provides opportunities to ...