The Synthetic and Biological Aspects of Prenylation as the Versatile Tool for Estrogenic Activity Modulation

Prenyl group is a ubiquitous structural moiety in natural compounds showing a wide spectrum of different biological activities with potential benefits for human health. This review presents the current knowledge on the prenylation of aromatic compounds such as flavonoids and coumarins. The references to the ‘classical’ methods that encompass Friedel‐Crafts reaction using prenyl alcohol and boron trifluoride, and alkylation with prenyl bromide in the presence of strong bases are given in comparison with the most state‐of‐the‐art prenylation methods. This review highlights the marked advance that has been achieved so far and makes prenyl group installment a versatile tool in the synthesis of drug candidates, natural compounds, and building blocks. Different aspects of prenyl group assembling methods are reported in more than 30 syntheses of natural substances and their analogues. The last part highlights a role of prenylation in flavonoid bioavailability and bioactivity modulation especially regarding their estrogenicity.