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Molecules 2004, 9(6), 394-404; doi:10.3390/90600394
Article

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

Received: 18 December 2003 / Accepted: 3 January 2004 / Published: 31 May 2004
(This article belongs to the Special Issue RACI 2003 symposium)
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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.
Keywords: Spiroacetals; bis-spiroacetals; oxidative radical cyclization Spiroacetals; bis-spiroacetals; oxidative radical cyclization
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Brimble, M.A. Radical Oxidative Cyclization of Spiroacetals to Bis-spiroacetals: An Overview. Molecules 2004, 9, 394-404.

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