Radical Oxidative Cyclization of Spiroacetals to Bis-spiroacetals: An OverviewAuthor(s): Margaret A. Brimble
Journal: Molecules ISSN 1420-3049
Volume: 9; Issue: 6; Start page: 394; Date: 2004;
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.