Toward the total synthesis of Ipomoeassin B

ORGN 731

Georgia Tsoukala, georgia.tsoukala@pharmacy.ac.uk1, Robert A. Falconer, r.a.falconer1@bradford.ac.uk2, and Mark Searcey, mark.searcey@pharmacy.ac.uk1. (1) Pharmaceutical and Biological Chemistry, The School of Pharmacy, University of London, 29-39 Brunswick Square, London, WC1N 1AX, United Kingdom, (2) The Institute of Cancer Therapeutics, University of Bradford, Richmond Road, Bradford, BD7 1DP, United Kingdom
Ipomoeassin B has been isolated from the leaves of Ipomoea squamosa and was found to exhibit highly potent cytotoxic activity against human ovarian cancer cell lines. It consists of a glucose-fucose disaccharide and three fatty acid side chains. Our synthetic approach involves orthogonal protection of glucose and fucose, disaccharide formation and sequential protecting group manipulation to incorporate the hydroxyester bridge and the unsaturated side chains. Progress toward the synthesis of Ipomoeassin B will be described.

 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

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