First total synthesis of (+)-schweinfurthins B and E

ORGN 710

Joseph J. Topczewski and David F. Wiemer, david-wiemer@uiowa.edu. Department of Chemistry, University of Iowa, The University of Iowa, Chemistry Building, Iowa City, IA 52242
The first total synthesis of (+)-schweinfurthin B, a potent and differentially active cytotoxic agent, has been achieved. Completion of the synthesis proceeded in 16 steps and 6% overall yield from commercially available vanillin. Key synthetic transformations included a Shi epoxidation, to introduce asymmetry, and an epoxide initiated cascade cyclization. The first total synthesis of the related compound (+)-schweinfurthin E also will be discussed.

 

Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009