Desymmetrization efforts towards fostriecin

ORGN 96

James P. McParland, jmcparl@ku.edu, Stephen R. Sieck, ssieck@ku.edu, Alan Whitehead, alanwh@ku.edu, and Paul R Hanson, phanson@ku.edu. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr, Malott Hall, Lawrence, KS 66045-7582
Efforts towards fostriecin are presented, focusing on two different tether-mediated desymmetrization strategies. In the first synthetic pathway, a tripodal coupling/multivalent activation strategy is utilized to assemble the key bicyclic phosphate, followed by selective reaction and cleavage methods. Overall, the phosphate moiety serves a multi-faceted role as a tether, leaving group, and protecting group. In the second approach, another variation on desymmetrization employing monosilylation, directed epoxidation and RCM presents a streamlined approach towards the natural product. Each pathway allows for myriad modifications and variations en route to fostriecin-like library development.

 

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

Sci-Mix
8:00 PM-10:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Sci-Mix

Division of Organic Chemistry

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