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The Aplysiatoxins: Reactions with Acid and Oxidants

Under the influence of ethanolic acetic acid the aplysiatoxins rearrange with retention of all carbon atoms. An osmate of the anhydrotoxins can be reduced to a glycol which resists oxidative cleavage but loses water and rearranges with acid. Consideration of PMR and reactivity data lead to partial assignment of relative stereochemistry of the toxins.