New approach toward a highly functionalized skeleton of Ingenol via a [6+4] cycloaddition

ORGN 572

James H. Rigby, jhr@chem.wayne.edu and Gaelle Chouraqui, gaelle@chem.wayne.edu. Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202
The key transformation in this totally new approach to the skeleton of Ingenol is the initial cycloaddition depicted in the following equation.

Clearly, the presence of the Z-alkene in the tether will greatly accelerate the reaction as evidenced by the precedent in the previous strategy. In addition, the diene is more electron rich. Finally it will lead to a more substituted skeleton of the title molecule. Our synthetic efforts towards the ABC core of Ingenol will be discussed.

 

New Reactions, Methodology, Total Synthesis, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 14 March 2005 Convention Center -- Sails Pavilion, Sci-Mix

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005