The Multistep Synthesis of a Chiral Aromatic Oxazoline (An Intermediate in the Synthesis of the Antibiotic Cytosporone E): An Advanced Undergraduate Laboratory Experience

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 11 Issue 2 (2006) pp 93-97

The Multistep Synthesis of a Chiral Aromatic Oxazoline (An Intermediate in the Synthesis of the Antibiotic Cytosporone E): An Advanced Undergraduate Laboratory Experience

Justin K. Wyatt,* Christopher L. Bolton, Marie C. Correia, and Caroline M. Watson

Department of Chemistry and Biochemistry, College of Charleston, 66 George Street, Charleston, SC 29424, wyattj@cofc.edu
Received September 9, 2005. Accepted November 3, 2006.

Published online: 22 February 2006

Abstract. An advanced organic chemistry laboratory for undergraduate students is described. The multistep synthesis is broken down into two parts. The overall four-step reaction sequence starts with L-valine and ends with a chiral aromatic oxazoline maintaining the integrity of the chiral amino acid. This is intended to be a “research-type” laboratory experience to introduce students to the process of conducting research.

Key Words: Laboratories and Demonstrations; organic chemistry; synthesis

(*) Corresponding author. (E-mail: wyattj@cofc.edu)

Article in PDF format (286 KB) HTML format

Supporting Materials:

Two supporting files are available. One contains the student assignments and handouts and the other contains the spectra. They may be downloaded in a Zip file (343 KB).