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Date of Award
Restricted Thesis: Campus only access
Bachelor of Science
Dr. John Gupton
Dr. Wade Downey
The development of naturally occurring compounds within a laboratory is important to society because it gives way for the mass production of a drug that has pertinent biological effects. In this research project, the ultimate goal is to create an easy, efficient, and flexible pathway to synthesizing Ninglain C, a naturally occurring compound in a marine organism. Ningalin C is part of the Ningalin family of compounds which exhibit anti-cancer activity because of their ability to reverse multi drug resistance1,3,5. Stemming from a six step process, a key intermediate, which will now be referred to as Ningalin C precursor, was synthesized. The pathway began with a commercially available compound, an analog of acetophenone, which led to the intermediate called a vinylogous amide. From there, haloenals and haloenoic acids were synthesized. Using Sonogashira-like conditions, a ring closure was performed and two steps later the Ningalin C precursor was made. Diverse functional groups were introduced throughout the scheme, which proved that this method is flexible and consistent.
Firich, Lauren, "Syntheses of key intermediates of ningalin C" (2013). Honors Theses. 143.