Recent Advances in the Chemistry of Quinolones

Abstract

The cyclization of 1,3-dicarbonyl dianions ('free dianions') and 1,3-bis-silyl enol ethers ('masked dianions') with various 1,2-dielectrophiles provides an efficient strategy for the synthesis of 2-alkylidenetetrahydrofurans, which represent useful synthetic building blocks. 2-Alkylidenetetrahydrofurans can be functionalized by lithiation and subsequent alkylation, NBS-mediated bromination and subsequent palladium-catalyzed cross-coupling, BBr3-mediated ring cleavage, elimination, dehydrogenation, palladium-catalyzed rearrangement, hydrogenation, Claisen rearrangements, and enzymatic kinetic resolution. © 2007 Elsevier Ltd. All rights reserved.