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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

Department of Chemistry, University of Auckland, 23 Symonds St., Auckland, New Zealand
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 (CC BY 3.0).
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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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