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Date of Award

Spring 2013

Document Type

Restricted Thesis: Campus only access

Degree Name

Bachelor of Science



First Advisor

Dr. John Gupton

Second Advisor

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.