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The Chemical Educator
ISSN: 1430-4171 (electronic version)
Abstract Volume 22
(2017) pp 66-69
Total Synthesis of Diabetes Drug Rosiglitazone for an Advanced Undergraduate Organic Chemistry Laboratory Course
Fehmi Damkaci*, Adam Szymaniak, and Ryan Cotroneo
Department of Chemistry, State University of New York at Oswego, Oswego, NY 13126, fehmi.damkaci@oswego.edu
Received August 15, 2016. Accepted September 27, 2016.
Published: 25 March 2017
Abstract. The total synthesis of racemic Rosiglitazone, also known as the anti-diabetes drug Avandia, in six steps is the basis for an advanced undergraduate organic chemistry laboratory course. Several techniques and concepts learned in an introductory organic chemistry laboratory course are reinforced, and include TLC analysis, recrystallization, and reaction work-up. Additional techniques introduced into the organic chemistry laboratory course include phase-transfer catalysis, flash column chromatography, pressurized hydrogenation reactions, and multi-step total synthesis. Students are challenged at several levels, but mostly by an expectation of independent, in-depth spectral analysis of each product and providing bi-weekly experimental reports with journal-style spectral analysis. An advanced undergraduate organic laboratory course centered on the total synthesis of a medicinally important compound provides an overall focus for the semester, as well as greater interest and motivation for students.s
Key Words: Laboratories and Demonstrations; organic chemistry
(*) Corresponding author. (E-mail: fehmi.damkaci@oswego.edu)
Article in PDF format (167 KB) HTML format
Supporting Materials:
Notes for instructors, experimental details, and 1H and 13C NMR spectra for all products are available as a PDF file. (11.3 MB)
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