The Application of Swern Oxidation: Synthesis of Dexamethasone (A Corticosteroid)

Noelia Luna

Co-Presenters: Individual Presentation

College: Hennings College of Science Mathematics and Technology

Major: BA.CHEM/PREPROF

Faculty Research Mentor: Stokes-Huby, Heather  Mongelli, Mathew

Abstract:

Swern Oxidation is a synthetic method of oxidizing primary and secondary alcohols to aldehydes and ketones, respectively. It uses oxalyl chloride and dimethyl sulfoxide with triethylamine as a base. Because this chemical reaction can occur under mild conditions, it is widely applied and a preferred method of oxidation in steroid synthesis. More specifically, it is used in the synthesis of corticosteroids; they are synthetic drugs that are prescribed as medications to reduce inflammation in the body. Although other oxidation methods can be applied such as Pyridinium Chlorochromate and Jones oxidation, challenges can arise during synthesis due to the requirement of higher temperatures, the use of strong of oxidizing agents and hazardous metals such as chromium. The purpose is to examine the overview of oxidation methods in steroid synthesis, but more specifically the application of the Swern Oxidation method in the synthesis of commercial pharmaceuticals and dexamethasone and the future direction of oxidation technology.