Abstract

Abstract Interest in the 1-azospiro(5.5)undecane ring system has increased dramatically due to the interesting chemical1 and neurophysiological2 properties of the toxins derived from the South American frog Dendrobates histrionicus, which contain this ring system. The principal alkaloid, histrionicotoxin, Ia, has resisted synthetic efforts3 to date, though the octahydro compound Ib has been prepared recently4, and there are three reported syntheses4,5 of the perhydro derivative Ic, which is an inhibitor of the ionic transduction system in synaptic membranes. In addition, several approaches to model compounds and potential synthetic precursors have been reported.6

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