Highly-substituted anthraquinone derivatives (HSAs) are a class of natural products found in a variety of fungal and plant species that have recently shown promise as antiviral, antidiabetic, anticancer and immune suppressing agents. Most currently available HSAs, including the natural product target Emodin, can only be acquired in milligram quantities via plant extraction. While several synthetic routes have been devised for the laboratory synthesis of specific anthraquinone derivatives, there are few general syntheses for HSAs, none of which provide a facile route to asymmetric derivatives. Here we present a straight-forward, generalizable approach to the synthesis of a variety of HSAs via the microwave-assisted condensation of benzoic acids. Conditions have been developed to achieve excellent yields on over a dozen rare and new HSAs, including asymmetric derivatives formed from the highly-selective cross-condensation of two different benzoic acids.<br/>

Synthesis and purification of highly substituted anthraquinones

255th National Meeting (2018)

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