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Radical Oxidative Cyclization of Spiroacetals to Bis-spiroacetals: An Overview

Author(s): Margaret A. Brimble

Journal: Molecules
ISSN 1420-3049

Volume: 9;
Issue: 6;
Start page: 394;
Date: 2004;
Original page

Keywords: Spiroacetals | bis-spiroacetals | oxidative radical cyclization

The use of iodobenzene diacetate and iodine under photolytic conditions provides and efficient method for the oxidative cyclization of spiroacetals bearing an hydroxyalkyl side chain to bis-spiroacetals. An overview is provided of the use of this reaction for the synthesis of several bis-spiroacetal containing natural products such as the polyether antibiotics salinomycin and CP44,161 and the shellfish toxins, the spirolides.
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