Total synthesis of (±)-Frondosin A

ORGN 467

Timo V. Ovaska, tvova@conncoll.edu, Xin Li, xli@conncoll.edu, Jonathan A. Sullivan, jasul@conncol.edu, and Alec E. Keon, aekeo@conncoll.edu. Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, CT 06320

Microwave-assisted oxyanionic 5-exo cyclization/Claisen rearrangement strategy has been applied to the generation of a variety of polycyclic, cycloheptane-containing ring systems which are widespread in nature and frequently of considerable medicinal interest. This tandem process was used as the key ring-forming step to construct an advanced 6-7 bicyclic intermediate, which served as a precursor to frondosin A, a natural product isolated from the marine sponge Dysidea frondosa.

 

Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- Rm. R05, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008