ORGN 162 |
| Previous work in our group has shown that oxadiazinones can serve as chiral auxiliaries in the synthesis of enantiomerically enriched compounds. We believe that this method may prove useful in the synthesis of (R)-arundic acid, which has been shown to be useful as a medicinal agent for the potential treatment of patients with mild to moderate Alzheimer's disease. To this end we have acylated the N3 position of (5S,6R)-4-isopropyl-5-methyl-6-phenyl-1,3,4-oxadiazinan-2-one with valeryl chloride, and carried out a series of asymmetric aldol reactions. Subsequent Corey-Kim reactions will convert the hydroxyl group of the aldol products into a bromide which can then be reductively removed. Optimization of hydrolysis will then yield the desired target compound. This poster will present current work towards the total synthesis of (R)-arundic acid. |
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |