Bis-guanidinium natural products, comprised of (+)-saxitoxin (STX), 11-saxitoxinethanoic acid (SEA), and zetekitoxin AB (ZTX), are a unique family of hydrophilic toxins that act by inhibiting the flow of ions through voltage-gated sodium ion channels (NaVs). Access to these molecules and derivatives thereof for studies of NaVs is only possible through de novo synthesis. Accordingly, efforts to prepare SEA and ZTX have been undertaken, with successful completion of the former target having been recently completed. Key steps in the preparation of this toxin include an oxidative annulation of an N-guanidyl pyrrole to form a five-membered cyclic guanidine and a base-catalyzed redox isomerization reaction. A new synthetic route is currently being developed to address challenges associated with assembling the more complex ZTX structure.

Synthetic studies on the bis-guanidinium toxins 11-saxitoxinethanoic acid and zetekitoxin AB

255th National Meeting (2018)

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