Phosphate tethers in synthesis: Efforts towards the total synthesis of fostriecin

ORGN 920

James P. McParland, jmcparl@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
Recent synthetic efforts towards fostriecin are presented. A tripodal coupling/multivalent activation strategy is utilized to assemble the key bicyclic phosphate, followed by selective reaction and cleavage methods to elaborate the highly functionalized natural product. The proposed pathway allows for myriad modifications and variations en route to fostriecin analogue library development. Overall, the phosphate moiety serves a multi-faceted role as a tether, multivalent activator, leaving group, and protecting group.