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.
Keywords: spiroacetals; shellfish toxins; pectenotoxins; spirolides; oxidative cyclization.
*Paper based on a presentation at the 16th International Conference on Organic Synthesis (ICOS-16), 11-15 June 2006, Mérida, Yucatán, México. Other presentations are published in this issue, pp. 153-291.