ORGN 708 |
| TamifluŽ is a potent inhibitor of influenza neuraminidase discovered at Gilead Sciences and co-developed by Hoffman-La Roche. This drug has recently received attention for its use as the primary treatment for avian bird flu in humans and has been stockpiled by governments around the world in the case of a pandemic. The existing industrial synthesis of this compound requires starting materials that are difficult to access, and multiple hazardous steps. Our goal is to achieve a diastereoselective synthesis of TamifluŽ from the easily accessible, acyclic starting materials, L-serine and 3-pentyloxyacetaldehyde. The route utilizes the stereochemistry of L-serine, protected as Garner's aldehyde, and takes advantage of an allenolate cyclization that has been utilized previously in our laboratory. Additionally, we propose expanding the scope of these allenolate cyclizations for other useful systems. |
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Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |