ORGN 486 |
| Matthias McIntosh and Wei Qi. University of Arkansas, University of Arkansas, 101 Chemistry Bldg, Fayetteville, AR 72701 |
| Abstract: Antascomicin-B is a macrolide isolated from a strain of Micromonospora that possesses structural similarities to FK506 and rapamycin and exhibits potent binding to FKBP12. Recent reports suggest that small molecule ligands of FKBP12 possess neuroprotective and neuroregenerative properties in mouse models of Parkinson’s disease. Our approach to the C22-C34 fragment of antascomicin-B will involve an Ireland –Claisen rearrangement to establish the C26 and C27 stereocenters. Directed hydrogenation will be used to install both the C29 and C23 stereocenters. Model studies have demonstrated the feasibility of the Ireland-Claisen rearrangement approach in generating the requisite pentadienoic acid. We will describe the details of the chemistry and further efforts to complete the synthesis of the model C22-C34 fragment. |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry |
