A new approach to (±)-heritonin. The preparation of β-tetralones from allylsilanes and acid chlorides

A new method for the preparation of 4-alkyl-β-tetralones is described, by reaction of arylacetic acid chlorides with allylsilanes. Employing β-tetralone 5, the synthesis of (±)-heritonine and (±)-epi-heritonine, natural piscicides isolated from Heritiera littoralis, was achieved in four steps and 22% overall yield. The key step of this synthesis involved the selenocarbenium ion-mediated elaboration of the butenolide ring of the natural product.