Total Synthesis of Aetokthonotoxin, the Cyanobacterial Neurotoxin Causing Vacuolar Myelinopathy
Manuel G. Ricardo, Markus Schwark, Dayma Llanes, Timo H. J. Niedermeyer, Bernhard Westermann
Abstract
Aetokthonotoxin has recently been identified as the cyanobacterial neurotoxin causing Vacuolar Myelinopathy, a fatal neurologic disease, spreading through a trophic cascade and affecting birds of prey such as the bald eagle in the USA. Here, we describe the total synthesis of this specialized metabolite. The complex, highly brominated 1,2'-biindole could be synthesized via a Somei-type Michael reaction as key step. The optimised sequence yielded the natural product in five steps with an overall yield of 29 %.
Topics & Concepts
NeurotoxinNatural productMetaboliteTotal synthesisPredationBiologyChemistryBiochemistryStereochemistryEcologyChemical synthesis and alkaloidsOxidative Organic Chemistry ReactionsAlkaloids: synthesis and pharmacology