ORGN 122 |
Enantioselective syntheses of phomopsolide E and analogs
| Miaosheng Li and George A. O'Doherty. C. Eugene Bennett Department of Chemistry, West Virginia University, 284 Prospect Street, 217 Clark Hall of Chemistry, WVU, Morgantown, WV 26506-6045 |
| A flexible, enantioselective route to highly functionalized α,β-unsaturated-δ-lactones has been applied to the synthesis of phomopsolide E and several analogs. This approach features the Sharpless catalytic asymmetric dihydroxylation on the dienone 4 and the Noyori catalytic asymmetric hydrogenation of furyl ketones 5 to produce the corresponding secondary alcohols in high enantioexcess, which can be stereoselectively transformed into α,β-unsaturated-δ-lactones by a short, highly diastereoselective oxidation and reduction sequence. 
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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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