ORGN 786 |
| Fumonisin B1(1) is a primary mycotoxin produced by the fungus Fusarium verticillioides. Due to its biological role as a sphingolipid biosynthesis inhibitor and structural similarity with sphingoid bases, we have accomplished its total synthesis. Our convergent approach utilizes new methodology based on oxonia-Cope rearrangements to stereoselectively synthesize the key coupling intermediates A and B. An efficient synthesis of the tricarballylic acid synthon C is another highlight of this approach. The synthetic design also enabled us to synthesize the hydrolyzed form of fumonisin B1, which also provides a starting point for exploring the structure-activity relationships of fumonisin analogs as anticancer agents.
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Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster
Division of Organic Chemistry |
