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The natural product chlorotonil displays high potency against multidrug-resistant Gram-positive bacteria and Plasmodium falciparum. Yet, its scaffold is characterized by low solubility and oral bioavailability but progress was recently made to enhance these properties. Applying late-stage functionalization, we aimed to further optimize the molecule. Previously unknown reactions including a sulfur-mediated dehalogenation were revealed.
Introduction Natural products represent an important pool of chemical diversity to cover the need of new scaffolds in drug discovery.1, 2 These scaffolds have the major advantage of displaying wider structural diversity than most synthetically obtained libraries including clinically approved drugs.3 This diversity is often derived from evolutionary optimization for biological activity, and in most cases cannot be easily accessed by classic organic synthesis.
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