ORGN 150 |
Suzuki reactions of alpha-halo enaminones and the asymmetric synthesis of Ipalbidine
| Xin Wang, Brandon J. Turunen, and Gunda I. Georg. Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045 |
| The results from Suzuki reactions between alpha-halo enaminones and various substituted aromatic boronic acids will be described. The reactions were carried out under reflux conditions and were compared with microwave-assisted reaction. The microwave-assisted reactions furnished the reaction products after shorter reaction times and in higher yields. The starting alpha-haloenaminones were prepared from enaminones using a modification of the Johnson procedure. The newly developed Suzuki reaction was subsequently applied to the asymmetric total synthesis of the indolizidine alkaloid Ipalbidine, a non-addictive analgesic natural product. Starting from homoproline, Ipalbidine was synthesized in 8 steps and in 12% overall yield. 
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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