Oxadiazinones as chiral auxiliaries: The asymmetric synthesis of a proposed hydroxyethyl isostere of a Human T-cell Leukemia virus (HTLV-1) protease inhibitor

ORGN 85

Raleigh W. Parrott II, rwparro@ilstu.edu and Shawn R. Hitchcock, hitchcock@xenon.che.ilstu.edu. Department of Chemistry, Illinois State University, Normal, IL 61790
Oxadiazinones are a family of chiral auxiliaries that have shown high diasteroselectivity with asymmetric aldol reactions. A persistent problem that occurs throughout several of the oxadiazinone systems is hydrolytic cleavage. Due to this issue, a new method for hydrolysis has been developed based on amine protecting group chemistry. Removal of the N4-substituent before hydrolysis may offer an advantage towards the success of hydrolytic cleavage at the N3-amide bond. After successful cleavage, the research will be directed towards the synthesis of a proposed hydroxyethyl isostere of a Human T-cell Leukemia (HTLV-1) protease inhibitor.
 

Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006