Total synthesis of C13-C14 cyclopropane discodermolide

ORGN 184

Ming Xian, mxian@sas.upenn.edu, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104 and Amos B. Smith III, Department of Chemistry, Monell Chemical Senses Center, and Laboratory for Research on the Structure of Matter, Univerisity of Pennsylvania, Philadelphia, PA 19104.
(+)-Discodermolide is a polyketide natural product displaying potent antimitotic activity. In parallel with our efforts to develop highly efficient synthesis of discodermolide, we have prepared a range of simplified and truncated analogs. As an extension to this work, we now report the total synthesis and cell-growth inhibitory activity of C13 (S), C14 (S)-cyclopropane discodermolide and C13 (R), C14 (R)-cyclopropane discodermolide.