Synthesis of novel Sansalvamide A derivatives

ORGN 150

Thomas J. Styers, tstyers209@yahoo.com, Rodrigo A. Rodriguez, Ahmet Kekec, ahmetkekec23@yahoo.com, Julia Cajica, Joe D. Brown, and Shelli R McAlpine. Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanille Drive, San Diego, CA 92182
Sansalvamide A is anticancer agent, and is composed of four hydrophobic amino acids and one hydrophobic hydroxy-acid. Described is the synthesis of forty-five Sansalvamide A derivatives. In addition, we describe novel reaction conditions that give high-yields for the insitu deprotections-cyclizations. Cyclizing large macrocycles is usually very challenging, and typically the yields are low (<25%). Despite structural and probable conformational differences, these new conditions cyclized twenty substrates in high yields. These conditions open the possibility for the synthesis of focused libraries in reasonable quantities of material, which is critical for biological assays.

 

Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Sci-Mix

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006