Three decades of disparlure and analogue synthesis

Abstract

In this review, we have described various syntheses of disparlure (a sex pheromone emitted by female gypsy moth) and its stereoisomers and analogues over the last three decades (1989–2020). The vast literature, chemical modifications and continuing interest in the synthesis and bioactivity study of this pheromone still go unabated. Most of the syntheses involve catalytic enantioselective methods and chiral pool approaches, while a few are based on the use of chiral auxiliary, chiral resolution and other methods. The racemic synthesis of disparlure and also the synthesis of various analogues including labelled molecules are covered here. A synthesis involving a direct enantiopure epoxidation of internal olefin would give the pheromone and its various analogues for different bioactivity studies and needs to be developed in future. The recent study has been directed toward labelled analogues for understanding the binding specificity shown by the pheromone binding proteins (PBP) and hence future directions could be to synthesize analogues that are more effective than the natural pheromone itself.