One-pot biomimetic synthesis of pimeforazine A and B from tyrosol, fluorescent benzoxazines with neuroprotective activity from the olive weevil Pimelocerus perforatus

A simple one-pot and biomimetic synthetic method for producing pimeforazine A and B, fluorescent benzoxazines with neuroprotective activity isolated from the olive weevil Pimelocerus perforatus, was developed. This synthesis uses the oxidation of commercially available 4-(2-hydroxyethyl)phenol (tyrosol) with 2-iodoxybenzoic acid (IBX), followed by the addition of concentrated aqueous ammonia. The reaction produced pimeforazines A and B in a ratio of 3.4:1, which is consistent with the natural product ratio. This method provides a practical and efficient alternative to extracting these compounds from the olive weevil.