Stereo-divergent synthesis as a tool for the stereochemical evaluation of the pladienolide B sidechain

ORGN 693

Alexander L. Mandel, amandel@ucsd.edu, Department of Chemistry and Biochemistry, University of California, San Diego, Department 0358, 9500 Gilman Dr, San Deigo, CA 92093-0358 and Michael D. Burkart, mburkart@ucsd.edu, Department of Chemistry and Biochemistry, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358.
A divergent route was developed that allows access to all putative stereoisomers of the pladienolide B sidechain. These sidechain stereoisomers were made spectroscopically distinct through cyclization into a natural fragment of pladienolide B degradation and compared to isolated pladienolide B to establish the absolute stereochemistry of the five stereocenters on the sidechain.
 

Total Synthesis of Complex Molecules
1:00 PM-5:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 132, Oral

Division of Organic Chemistry

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