Novel and Efficient Synthesis of the Promising Drug Candidate Discodermolide
Final rept. 1 Feb 2008-31 Jan 2010
STATE UNIV OF NEW YORK AT STONY BROOK RESEARCH FOUNDATION
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In a novel approach to the potential antitumor drug discodermolide, we have prepared new stereotriad building blocks and used them to build one of two key intermediates. We prepared the other critical intermediate, the so called stereopentad, by degradation of oleandomycin. We also modified the building block synthesis in order to prepare anti, anti stereotriads and we developed a new route to polypropionate building blocks that bear a Z-vinyl iodide or an E-vinyl iodide. We showed that proper choice of catalyst allows the reduction of a propargyl alcohol to a Zallylic alcohol in the presence of a vinyl iodide. Thus we have shown the viability of all high-risk steps in the total synthesis.