Synthesis of Asebogenin and Balsacone A Precursor by a Novel Synthetic Strategy: Recent Opportunities for and Challenges of Total Synthesis of Balsacone A

Abstract

One of the main areas of interest of synthetic organic chemistry is the rapid construction of small molecules with proven diverse biological activities for the development of new strategies to cure human health. In particular, the development of novel synthetic strategies is the most important option for reaching the molecular scaffolds of active molecules of natural origin. Balsacone A and asebogenin are compounds that exhibit a wide variety of important biological activities. In this respect, it has become very important to develop new strategies for the construction of biologically active natural and synthetic balsacone analogues. In particular, balsacone derivatives with hydroxy-substituted dihydrochalcone skeletons can be isolated from plant sources or obtained by hemi-syntheses using bio-sourced precursors. An efficient synthetic strategy to synthetically obtain balsacone A is the aim of the present study that considers the limited natural availability of these molecules as well as other factors, such as cost and time. Starting with phloroglucinol, a nine-step synthesis of the precursor of balsacone A was achieved at a 10% overall yield. Furthermore, asebogenin, which has a dihydrochalcone structure and plays a key role in the synthesis of balsacone A, was synthesised with a good yield.

Keywords

• dihydrochalcone
• natural product synthesis
• asebogenin
• balsacone A