ORGN 176 |
| Recently, it was announced that ISO-1 (methyl 3-(p-hydroxyphenyl)-5-Δ2-isoxazolinylacetate) inhibits the production of macrophage migration inhibitory factor. This antagonism results in suppression of the development of hyperglycemia and can be a possible therapeutic pathway for the treatment for diabetes. We have investigated a synthetic route to ISO-1 and its derivatives via the palladium-mediated nucleometalation / methoxycarbonylation of β,γ-unsaturated oximes. This novel route to this class of compounds is tolerant of a wide variety of functionality in the starting material, and provides a rapid route to highly functionalized isoxazolines. Syntheses for a series of derivatives of this class of compounds, the proposed mechanism and scope of the palladium-mediated cyclization, and details on the spectroscopic identification of the Δ2-isoxazoline ring system will be discussed.
|
|
Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster
Division of Organic Chemistry |
