Progress towards the total synthesis of tautomycetin and the development of chiral N-aminoaziridine hydrazones as auxiliaries for the synthesis of deoxypolypropionate units

ORGN 577

Cristiana A. Zaharia, czaharia@uci.edu and A. Richard Chamberlin, archambe@uci.edu. Department of Chemistry, University of California, Irvine, 516 Rowland Hall, Irvine, CA 92697
Tautomycetin, isolated from the fermentation broth of Streptomyces griseochromogenus is a potent and selective protein phosphatase inhibitor. Synthetic studies toward the total synthesis of tautomycetin will be described. One of the structural features of this natural product is a deoxypolypropionate unit, which will be synthesized using a highly convergent strategy developed in our lab. This method consists of two sequential alkylations of trans-diisopropyl N-aminoaziridine hydrazone, which allows the elongation of the hydrocarbon chain in both directions.

 

New Reactions, Methodology, Total Synthesis, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 14 March 2005 Convention Center -- Sails Pavilion, Sci-Mix

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005