ORGN 53 |
| The synthesis of mitomycin compounds is typically costly and involves many intermediate compounds that are produced in moderate yields. A novel synthesis of the ring system that is the backbone of all the mitomycins has been developed. Our research utilizes an A-B-C-D approach to the synthesis of the tetracyclic fused ring system, beginning with a vinyl azide rearrangement to the indole backbone. A key step in the synthesis involves the intramolecular cyclization of the C-ring. Methods used to tackle this challenging cyclization process will be discussed. Several olefin aziridination techniques are available to complete the synthesis of the D-ring. The proposed synthetic approach increases the overall yield and reduces the number of steps necessary to generate the target molecules. Progress towards the synthesis of the mitomycin skeleton and other mitomycin analogs will be presented. |
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Heterocycles and Aromatics
1:00 PM-5:20 PM, Sunday, 26 March 2006 Georgia World Congress Center -- C301, Oral
Division of Organic Chemistry |