ORGN 435 |
| Danielle L. Aubele and Paul E Floreancig. Department of Chemistry, University of Pittsburgh, Box 110, 219 Parkman Ave., Pittsburgh, PA 15260 |
| Recently we have reported that the ionization of acetals in Lewis acidic micelles leads to intermediate oxocarbenium ions which undergo efficient and stereoselective Prins cyclization, in preference to hydrolysis, resulting in the formation of cis-2,4,6-trisubstituted tetrahydropyrans. The utility of this method is demonstrated through its application to a highly convergent total synthesis of the marine macrolide (+)-Dactylolide. The cis-2,4,6-trisubstituted tetrahydropyran core of the molecule arises from the acetal precursor for intramolecular Prins cyclization which results from the condensation of two highly functionalized enantio-pure fragments, 1 and 2. |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry |
