Recent insights into anatoxin-a chemical synthesis, biomolecular targets, mechanisms of action and LC-MS detection

• Published in: Phycotoxins pp. 137 - 180
• Main Authors: Fonseca, Custódia, Aureliano, Manuel, Abbas, Feras, Furey, Ambrose
• Format: Book Chapter
• Language: English
• Published: United Kingdom John Wiley & Sons, Incorporated 2015; Wiley; John Wiley & Sons, Ltd
• Subjects: anatoxin‐a (ANTX‐a); liquid chromatography (LC)‐MS detection; neurotoxicity
• ISBN: 9781118500361; 1118500369
• DOI: 10.1002/9781118500354.ch7

Anatoxin‐a (ANTX‐a) is a toxin well known to induce neurotoxicity. There have been several synthetic pathways to obtain ANTX‐a, and these are briefly described in this chapter. It is possible to separate into categories the different total synthesis approaches to ANTX‐a, according to the methodology used: (a) Synthesis of ANTX‐a via ring expansion of tropanes (b) Synthesis of ANTX‐a via transannular cyclization of cyclooctenes (c) Synthesis of ANTX‐a via iminium salts (d) Synthesis of ANTX‐a via an enol (e) Synthesis of ANTX‐a via nitrones (f) Synthesis of ANTX‐a via allene (g) Synthesis of ANTX‐a via tandem reactions and (h) Synthesis of ANTX‐a via enine metathesis. Liquid chromatography (LC)‐UV methods were developed to determine ANTX‐a, but this approach was inhibited by the presence of interferences in samples. Anatoxin and its analogues have been the subject of scientific research in different areas.