Abstract
This thesis is composed of reports on two projects, which are described separately in two chapters.
The first project described (Chapter 1) involves the synthesis of a series of molecules that contain a 1,4-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxy-imide core structure. These types of molecules represent a class of analogues of the natural product cantharidin, a potent cytotoxic agent isolated from Meloidae insects. Cantharidin and cantharidin-like small molecules have been extensively studied in literature as potential leads in new anti-cancer medications. A series of 1,4-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3- dicarboxy-imides are also being investigated by researchers at Bristol-Meyers-Squibb (BMS) as prospective treatments of prostate cancer (PC). PC is the most common malignancy among men in the United States and the second most common cause of cancer-related death worldwide. The need for novel prostate cancer medications arises from patient resistance to current PC drugs. Synthesis and biological activity of a series of cantharidin/BMS-641988 analogues will be presented. Theoretical studies to identify our next generation of synthetic targets and their potential application in the treatment of PC will also be discussed.
The second project (Chapter 2) describes new methodology studies to provide access to 9-membered lactones. This structural moiety is an unusual, yet frequently observed structural feature of natural products. The synthesis of medium sized cyclic functional groups, namely 9-membered lactones, is still a formidable challenge in synthetic organic chemistry. Studies toward a facile, three step synthesis of molecules containing 9-membered lactones is proposed and synthetic efforts towards the appropriate precursors will be discussed.
Library of Congress Subject Headings
Diels-Alder reaction; Biomolecules--Synthesis
Publication Date
5-8-2019
Document Type
Thesis
Student Type
Graduate
Degree Name
Chemistry (MS)
Department, Program, or Center
School of Chemistry and Materials Science (COS)
Advisor
Jeremy A. Cody
Advisor/Committee Member
Christina Goudreau Collison
Advisor/Committee Member
Douglas J. Tusch
Recommended Citation
DeCicco, Ethan Michael, "Using the Diels-Alder Reaction in the Synthesis of Biologically Interesting Molecules: Targets of Opportunity" (2019). Thesis. Rochester Institute of Technology. Accessed from
https://repository.rit.edu/theses/10106
Campus
RIT – Main Campus
Plan Codes
CHEM-MS
