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Total Synthesis of Dithiodiketopiperazine Natural Products

Marshall Liss, speaker
Marshall Liss
Graduate Student, Department of Chemistry
University of Georgia
Chemistry Building, Room 400
Organic Seminar

Dithiodiketopiperazines or “DKP’s” is common motif that appears in various natural products. These natural products have been shown to display anti-viral or anti-tumor properties. Within the past two decades, an increasing number of natural products have been isolated containing a DKP core. Although synthetic strategy towards this core has been around since the 1960’s, there is still much innovation withing the area of DKP natural product total synthesis. This seminar discusses three recent total syntheses of natural products containing a DKP core, including K.C. Nicolaou’s work on Epicoccin G in 2011, Sarah Reisman’s work on Acetylaranotin in 2012, and, lastly, a much more recent synthesis of Acetylaranotin from Olivier Baudoin in 2019.

Diagrams of rostratin A (colon cancer inhibitor), acetylaranotin (viral-RNA synthesis inhibitor, and epicoccin G (HIV-1inhibitor)

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