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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

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.