ORGN 392 |
| With the aim of further understand the conformational preferences of the kinases involved in the activation of the anti herpes simplex virus 1 (HSV-1) agent, North-MCT (1), a new thymidine analog (2) was designed and synthesized for optimal interaction with HSV-1 thymidine kinase. In order to do so, the compound was built with the antipodal South conformation, the base in the anti disposition, and a with repositioned hydroxyl group capable of mimicking the 3'-OH of a conventional nucleoside. The enantioselective synthesis of 2 was achieved through a linear approach, starting from the known cyclopentenone (-)-3. A Baylis-Hillman reaction was employed for the introduction of the hydroxymethyl side chain and a regioselective nucleophilic opening of a cyclic sulfite was used in order to obtain the desired regioisomer (4) with the required trans disposition of the oxygenated and nitrogenated functionalities on the carbocyclic ring.
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New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Sci-Mix
Division of Organic Chemistry |
