A Study and Attempted Synthesis of a Carbocyclic Nucleoside Precursor Via a Chiral Aziridine

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John Klassen


Carbocyclic nucleosides have shown promise in treating the AIDS virus and cancer. These molecules terminate DNA replication, thereby preventing the cancer from spreading, in addition to being more stable in the body. For this reason, a highly functionalized cyclopentane ring with three chiral centers would be useful for synthesis of these sorts of molecules. Aziridines offer a means for attaining these goals. Their chemistry is very similar to epoxides, but aziridines offer the advantage of maintaining the nitrogen functional group. Using intramolecular ring opening of the aziridine can be used to form the cyclopentane ring. In the attempted synthesis, L-aspartic acid was the starting material. The addition to the tosylate activating group to the aspartic acid proved difficult to perform. A problem was also encountered later in the reduction of a lactone.