Enantioselective synthesis of a 15-F2-isoprostane and an isoprostanylphospholipid

ORGN 694

Manami Shizuka, shizuka@bc.edu and Marc L. Snapper. Department of Chemistry, Boston College, 2609 Beacon St., Chestnut Hill, MA 02467
The enantioselective total synthesis of a biologically active lipid metabolite, ent-15-epi-F2t-isoprostane (1), is described. The key sequence involves a regioselective olefin cross metathesis of a highly functionalized, enantiomerically enriched divinyl cyclopentyl intermediate. This route has allowed us to synthesize other derivatives, including an an isoprostanyl phospholipid (2) – a possible intermediate in the biosynthesis of the isoprostanes.

 

Total Synthesis of Complex Molecules
1:00 PM-5:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 132, Oral

Division of Organic Chemistry

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