ORGN 84 |
| 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 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. This oxadiazinone provides high diastereoselectivity in the subsequent asymmetric aldol reaction, however, cleavage of the aldol adduct from the N3 position has been difficult. To help alleviate this problem, we propose that a novel oxadiazinone with an N4-[2-pyridylmethyl] substituent might improve the cleavage of the desired product from the oxadiazinone ring system. This poster will present current work towards the total synthesis of (R)-arundic acid and the N4-[2-pyridylmethyl] substituted oxadiazinone.
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Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Sci-Mix
Division of Organic Chemistry |