Synthetic approaches to the allosamidin disaccharide

ORGN 83

Rena Bodner, ra2016@barnard.edu, Bridget K. Marcellino, bm2021@barnard.edu, Alexandra Severino, as2039@barnard.edu, and Christian M. Rojas, crojas@barnard.edu. Department of Chemistry, Barnard College, 3009 Broadway, New York, NY 10027
Progress toward the synthesis of the disaccharide portion of the potent chitinase inhibitor allosamidin will be described. Our strategy employs rhodium(II)-catalyzed oxidative cyclization of allal 3-carbamates for preparing and linking the 2-amido-2-deoxy-β-allopyranoside subunits of the disaccharide. Incorporation of an n-pentenyl glycoside as a reducing end cap makes the synthetic approach amenable to subsequent preparation of allosamidin analogs.
 

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, 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