Functionally-active phosphate tethers: Progress towards the synthesis of dolabelides

ORGN 97

Joshua D. Waetzig, jwaetzig@ku.edu, Alan Whitehead, alanwh@ku.edu, and Paul R Hanson, phanson@ku.edu. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045
Current progress towards the dolabelide class of natural products via functionally active phosphate tethers (P-tethers) is described. The dolabelide family of natural products represents a class of potent poly-ketide based macrolactones that exhibit a wide range of biological activity. We have recently reported the formation of P-chiral bicyclic phosphates via a terminus differentiation strategy utilizing RCM for the desymmetrization of phosphate tethered 1,3-anti-diols. This study focuses on the extension of this chemistry to the specific generation of both the northern and southern portions of dolabelide via both antipodes of the 1,3-anti-diol derived bicyclic phosphates.