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

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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

ABSTRACT
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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