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Pure Appl. Chem., 2007, Vol. 79, No. 2, pp. 153-162

Synthetic studies toward shellfish toxins containing spiroacetal units

Margaret A. Brimble and Rosliana Halim

Department of Chemistry, University of Auckland, 23 Symonds Street, Auckland, New Zealand

Abstract: The synthesis of the ABC spiroacetal-containing fragment of the marine biotoxins, the pectenotoxins (PTXs), is described. The synthetic strategy involves appendage of the highly substituted tetrahydofuran C ring to the AB spiroacetal unit via stereocontrolled cyclization of a γ-hydroxyepoxide. The bis-spiroacetal moiety of the spirolide family of shellfish toxins is also described, making use of an iterative radical oxidative cyclization strategy.