Pahutoxin: Synthesis and Determination of Its Absolute Configuration

Absolute Structure and Total Synthesis of Lipogrammistin-A, a Lipophilic Ichthyotoxin of the Soapfish

“…1-3 These toxic secretions clearly function as a chemical defense against predators and other enemies. However, the chemical components of these ichthyotoxins have been elucidated in only a very few cases; e.g., pahutoxin, a choline ester of 3-acetoxypalmitic acid from the Hawaiian boxfish Ostracion lentiginosus, 4,5 and pardaxins (peptides) and pavoninins (steroid glycosides) from the two soles Pardachirus pavoninus and P. marmoratus. [6][7][8][9][10] Soapfish, another well-known ichthyocrinotoxic family, are known to secrete copious amounts of mucus, which produces a soaplike foam in water.…”