| Summary: | 碩士 === 正修科技大學 === 化工與材料工程研究所 === 95 === This study used cis-2-butene-1,4-diol as a starting material to synthesize shikimic acid and was carried out in three steps to give olefin, and then reacted with ethyl acrylate to undergo [4+2 ] Diels-Alder reaction. In this stage, a six-membered ring intermediate precursor of shikimate was obtained and its stereochemistry was carefully controlled. In development of the cis-dihydroxylation reagents, complex was first formed by reacting dioxzole derivatives with the iron complex, followed by addition of hydrogen peroxide as a catalyst to undergo cis-dihydroxylation reaction.
In synthesis of Tamiflu, asymmetric addition of [4+2] Diels-Alder reaction was carried out with pyrrole and ethyl acrylate by asymmetric catalyst to produce a six-membered ring intermediate. In order to obtain correct relative stereo-orientation between C3 and C4 on the six-membered ring, a biycyclo compound was used to hinder cis-dihydroxylation with steric effect.
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