Natural products are a category of organic materials that encompass many and/or all materials produced by living things. These compounds have evolved over time for a specific function to benefit the organism, and they are targeted by medicinal chemists as starting scaffolds for drug discovery. Specifically, medicinal chemists often target secondary metabolites (e.g. alkaloids), a subclass of natural products that act upon organisms outside of the producer. The diketopiperazine core is common among secondary metabolites, since the structure is readily synthesized from amino acid precursors. The 2,5-diketopiperazine core is found in many therapeutic compounds that have beneficial effects. Different isomers of diketopiperazine are also being studied for biological activity. One of the isomers, 2,3-diketopiperazine, has been targeted by medicinal chemists due to possible biological activity, but it remains underexplored. The 2,3-diketopiperazine core structure is present in three new natural products, orychophragines A-C, that have been isolated from <i>O. violaceus</i>. These newly found alkaloid compounds have anticancer activity, and they represent a family of natural products that hold possibilities for additional biological activities that may be useful in the pharmaceutical and medicinal chemistry fields. Currently, no total synthesis of these molecules exists. For continued and more accessible biological study, it is imperative to have successful synthetic routes to orychophragine compounds. Progress on synthesizing orychophragine A from commercially available L-serine will be detailed. Protecting strategies and synthetic traps will be highlighted. In addition, preliminary evaluation of key intermediates for acetylcholinesterase inhibition and antibacterial properties will be discussed.

Synthetic routes towards orychophragine A

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.