Natural products have played a significant role in drug discovery and from a synthetic perspective, allow for complex, unique scaffolds to be obtained in large quantities at a low cost. However, many natural products remain to be underexplored. Stevioside, which is extracted from the Stevia plant, <i>Stevia rebaudiana</i>, can be hydrolyzed by acid to form isosteviol. Isosteviol derivatives have a range of different biological activities such as anti-inflammatory, inhibition of alpha-glucosidase, anti-cancer, anti-tuberculosis, and inhibition of hepatitis B. Isosteviol is a tetracyclic diterpenoid with a cyclic ketone and external carboxylic acid. These functional groups can be selectively manipulated through different chemistries – click chemistry, ring closing metathesis, peptide chain synthesis and Ugi reactions. We report on the synthesis of several peptidic and macrocyclic isosteviol analogs developed through the use of Ugi reactions and ring closing metathesis, respectively. The antibacterial and anticancer activity of this class of natural product analogs will be presented.

Isosteviol: Natural product building block for potential therapeutic agents

ACS Spring 2022

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