Non-amino acid approach to 2-thiazolines

ORGN 732

Valerie Ann Cwynar and Edwin Vedejs. Department of Chemistry, University of Michigan, 730 N. University Ave., Ann Arbor, MI 48109
Amino acids are the traditional starting materials for the preparation of 2-thiazolines. This presents a limitation on the substituents that may be incorporated into the heterocycle, and thus a non-amino acid approach for 2-thiazolines has been developed. The approach utilizes a process that resembles a Heine rearrangement between a thionoester and a terminal aziridine to access the 2-thiazoline products (eq. 1). We plan to integrate this approach, with incorporation of appropriate functinalization, in our synthesis of (R)-telomestatin. Additionally, we have prepared bis-oxazoles from C(4)-metallated oxazoles and di-halogenated oxazoles via palladium(0) catalysis (eq. 2).

 

Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009