Toward the total synthesis of (-)-uprolide D

ORGN 788

CÚline A Griot, cag9w@virginia.edu and James A. Marshall. Department of Chemistry, University of Virginia, McCormick Road, P.O Box 400319, Charlottesville, VA 22904
(-) Uprolide D, a cembranolide isolated from gorgonian Eunicea mammosa displays cytotoxic activity against HeLa cells (IC50= 5.0 mg/mL = 0.0143 mmol/mL). The limited supply (0.001% of extract) of (-)-uprolide D makes it interesting target for synthetic effort. (-)-Uprolide D contains several challenging structural elements that must be overcome to achieve a total synthesis of this molecule. The cembranolide contains an oxygen bridged 14-membered ring, an embedded tetrahydrofuran ring, a fused γ-lactone as well as seven stereocenters. To date, no total synthesis of (-)-uprolide D has been reported. A plan was developed for the total synthesis of (-)-uprolide D utilizing a convergent synthesis. One of the key steps would be the simultaneous formation of the macrocycle and the fused γ-lactone.

 

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