Catalytic asymmetric protocols for the enantioselective synthesis of 3(2H)-furanones

ORGN 309

Charles M Marson, c.m.marson@ucl.ac.uk1, Esra Edaan1, James M Morrell1, Simon J Coles2, Michael B Hursthouse2, and David T Davies3. (1) Department of Chemistry, University College London, Christopher Ingold Building, 20 Gordon Street, London, United Kingdom, (2) EPSRC UK National Crystallographic Service,School of Chemistry, University of Southampton, Highfield, Southampton, (3) Department of Medicinal Chemistry, GlaxoSmithKline, Gunnels Wood Road, Stevenage, United Kingdom
The 3(2H)-furanone ring system is found in a variety of natural products including potent anti-tumor agents. As part of our program to develop new catalytic routes to oxygen heterocycles, we will describe a new catalytic sequence (shown below) to 3(2H)-furanones in 92-97% ee by means of the asymmetric dihydroxylation of enyones. In certain cases, the 3(2H)-furanones can be prepared from enynones by a domino process in which dihydroxylation followed by cyclisation occur in one operation. 3(2H)-furanones are versatile precursors useful for the synthesis of natural products containing the dihydrofuran or tetrahydrofuran ring; application of the new protocol to the synthesis of a natural product will be described.

 

Asymmetric Reactions and Syntheses
1:00 PM-5:00 PM, Monday, 11 September 2006 Moscone Center -- Room 131, Oral

Division of Organic Chemistry

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