Preparation of phenyl-butyraldehydes using a base-catalyzed aromatization of dienones

Abstract

Seven aldehydes were prepared using a five-step sequence synthesis. The synthetic strategy involved the use of a novel aromatization reaction of dienones. These key intermediates were prepared following a sequence involving BAR of substituted tetralones, ketones reduction, protection of alcohol, and bis-allylic oxidation. The key step of the route is an aromatization promoted by basic reaction conditions of dienones leading to substituted 4-phenyl butanals.