Date of Graduation

Fall 12-2017

Document Type


Degree Name

Master of Science in Chemistry


College of Arts and Sciences



First Advisor

Megan Bolitho


Quorum sensing is a system that facilitates bacteria turning on and off gene expression depending on population density. System 2 quorum sensing is utilized by both Gram positive and Gram negative bacteria, and the quorum sensing molecule used in this system is AI-2. AI-2 is biosynthesized by the enzyme LuxS from the precursor SRH. This thesis describes an improved synthesis of SRH through the exploration of different protecting group strategies. The knowledge gained from the improved synthesis of SRH is then applied toward the synthesis of SRH analogues with increased steric bulk installed through use of a stereoselective anti-Mannich reaction. SRH analogues with increased steric bulk are hypothesized to act as inhibitors of LuxS – with the ultimate goal decreasing the amount of AI-2 in the environment and therefore silencing gene expression dependent on system 2 quorum sensing.