| Summary: | 碩士 === 臺灣大學 === 化學研究所 === 98 === Influenza has endangered human for a long time. Anti-influenza drugs are regarded as the last line of defense against influenza pandemics. Tamiflu, one of neuraminidase inhibitors, has been a popular drug for influenza therapy. However, the newly-mutated influenza viruses have strong resistance against Tamiflu. Thus, new drugs are needed for new influenza viruses.
Tamiphospor is one of candidates for anti-influenza drugs. In 2007, our group has used D-xylose as a starting material to synthesize Tamiflu, Tamiphosphor (a phosphonate congener), and the guanidine derivative. Both Tamiphosphor and its guanidine derivative are more potent than Tamiflu.
However, some problems such as yielding side products were encountered when we tried to synthesize these drugs in a large scale. In this thesis, I focus on how to improve the efficiency of synthesis from D-xylose. By retrosynthetic analysis, I change the sequence of synthesis by using a diprotected amine as the key intermediate, and thus successfully carry out the formal synthesis of both Tamiflu and Tamiphosphor.
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