CHED 404 |
| Salinosporamide A is an actinomycete bacterium from the S. tropica strain of Salinispora. It has been found that this complex is a good proteasome inhibitor and can specifically target three activities of the 20S proteasome including inhibibition of the proteasome's ability to regulate how substances are broken down, cell survival and growth of tumor cells. Both Corey and Danishefsky have developed total syntheses of 1. We have discovered a new base-catalyzed tandem aza-Payne rearrangement/hydroamination reaction that proceeds with excellent control of diasteroselectivity. This reaction allows us to access a highly functionalized pyrrolidine core 4 that we propose to utilize in a synthesis of an advanced intermediate in Corey's total synthesis of 1. We will also report on our progress on expanding the scope of the hydroamination reaction by varying the substituents on the aziridine, changing the R' group of the acetylide, and optimizing the ylide equivalents and reaction temperature.
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Chemical Education |
