Synthesis of enantiopure isoxazolidine monomers for β3-oligopeptide synthesis in water

ORGN 136

Justin A. Russak and Jeffrey W. Bode, bode@chem.ucsb.edu. Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, CA 93106-9510
We have recently shown that β3-oligopeptides can be synthesized by peptide couplings of α-ketoacids and isoxazolidines. This process occurs without reagents, side-chain protecting groups, or reaction byproducts. The isoxazolidine monomers can be easily synthesized in enantiopure form from readily available starting materials and with little to no chromatography. The key reaction is a one-pot 1,3-dioplar cycloaddition of nitrones derived from carbohydrate-based chiral auxiliaries and aldehydes. These in situ generated nitrones react with methyl 2-methoxyacrylate to give the isoxazolidines with excellent regio- and stereoselectvity. The synthesis of a wide variety of β3-peptide monomers will be presented.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006