A facile synthesis of (±)-heliannuol-D

Abstract

A facile synthesis of (±)-heliannuol-D 1, which serves as an allelopathic chemical in nature and a potential lead compound in the search for new herbicides, has been achieved in a linear 11 steps, together with its epimer. The synthesis commenced with 4-methoxy-3-methyl-acetophenone, through the Baeyer-Villiger reaction, lithiation and addition, epoxidation and intramolecular cyclization to give (=)-heliannuol-D (1) and its epimer (1a) in 32.6% overall yield. Our synthetic approach is cost-effective; this will be helpful in applying this kind of compound for the development of a new generation of agrochemicals.