Total Synthesis of Prenylated Isoflavone Natural Products

Abstract

Prenylated phenols constitute a prominent class of natural products commonly found in plants and fungi that demonstrate many biological effects. In general, relative to their corresponding non-prenylated parent phenol compound, phenols bearing -prenyl, -geranyl, or - farnesyl substituents tend to show enhanced bioactivities, potentially due improved cell permeation associated with greater lipophilicity. Five prenylated isoflavone natural products: corylifol A, neobavaisoflavone, myrsininone A, isowighteone, and methyl corylifol A are isolated from distinct fungal or plant species and associated with diverse biological profiles. These natural products are of interest due to their demonstrated biomedical potential. Many isoflavones and other prenylated flavonoids exhibit excellent antioxidant and anticancer activity. These isoflavone natural products, along with five related novel compounds are synthesized using regioselective ortho-allylation of phenolic boronic ester mediated by acidic alumina, followed by a Suzuki cross- coupling with a functionalized chromone.