Progress toward the synthesis of (-)-dictyostatin and 16-normethyldictyostatin

ORGN 414

Andrew K. Dilger, dilger@chem.wisc.edu, Vijay Gopalsamuthiram, vijay@chem.wisc.edu, and Steven D. Burke, burke@chem.wisc.edu. Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave., Madison, WI 53706
Progress toward the synthesis of the macrolide natural product (–)-dictyostatin and its 16-normethyl analogue will be presented. In particular, a two-directional strategy to access a precursor to the C11-C23 segment via C2-symmetric intermediates has been accomplished. This approach utilizes an enantioselective double hetero Diels-Alder reaction and a kinetically-controlled, highly diastereoselective Meerwein-Ponndorf-Verley reduction. This three-step sequence efficiently installs ten stereogenic centers, seven of which occur in the natural product. Efforts to desymmetrize and elaborate this precursor will also be discussed.

 

New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007