Progress toward the total synthesis of psymberin

ORGN 918

James R. Davies, jrdavies@chemistry.ucsc.edu, Yakira R. Landaverry, Sandra Ast, Kirsten Milinkevich, Brian S. Gerstenberger, gerstenb@chemistry.ucsc.edu, and Joseph P. Konopelski, joek@chemistry.ucsc.edu. Department of Chemistry and Biochemistry, University of California Santa Cruz, 1156 High Street, Santa Cruz, CA 95064
Psymberin (1), a natural product extracted from the sponge Psammocinia sp. (Dictyoceratida, Irciniidae) by Prof. Phil Crews and co-workers from the waters of Papua New Guinea, was found to have potent activity against solid tumors. Structurally, psymberin is very similar to compounds found in the pederin family. This similarity has been the guide for our efforts to create a viable synthetic route to the natural product and a small library of isomeric compounds. The proposed convergent synthesis consists of three fragments. Our route plans to utilize fluorous tagging, a practice developed by Prof. Dennis Curran, to synthesize the natural product plus seven isomers of psymberin (representing all possible stereoisomers at C4, C16 and C17) in one batch. The isomers will then be separated based on fluorous content. (NIH Grant: CA98878, GM58903-05)

 

Total Synthesis of Complex Molecules
1:00 PM-5:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 134, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006