CHED 405 |
| Alkaloids that are structurally similar to sugars are attractive as synthetic targets because many have shown promise as glycosidase inhibitors. Our efforts directed toward synthesizing certain natural and unnatural pyrrolizidine alkaloids required the synthesis of a number of amino alcohols. To construct these alcohols, carbon nucleophiles were reacted with a proline-derived aldehyde. In order to rigorously determine the stereochemistry of the addition, the product allylic alcohols were converted to the corresponding oxazolidinones. The relative stereochemistry of the oxazolidinones could then be determined by 2-D NMR experiments. Results of the carbonyl addition and cyclization reactions are presented and the carbonyl addition stereochemistry is discussed in the context of models used for predicting diastereoselectivity in these types of reactions.
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Undergraduate Research Poster Session: Organic Chemistry
11:15 AM-1:15 PM, Monday, 14 March 2005 Convention Center -- Hall D, Poster
Division of Chemical Education |
