莽草酸
产量(工程)
环氧化物
奎宁酸
化学
乳糖
衍生工具(金融)
有机化学
立体化学
内酯
催化作用
材料科学
金融经济学
经济
冶金
作者
Muriel Cordon Federspiel,Rolf Fischer,Michael Hennig,Hans-Jürgen Mair,Thomas Oberhauser,Gösta Rimmler,Thomas Albiez,J. Bruhin,Heinrich Estermann,Carsten Gandert,Volker Göckel,Stephan P. Götzö,Ursula Hoffmann,G. Huber,Günter Janatsch,Stephan Lauper,Odette Röckel-Stäbler,and Rene Trussardi,Andreas G. Zwahlen
摘要
Starting from (−)-quinic acid, the title compound was synthesized in seven chemical steps and an overall yield of 35−38%. The route of the improved Gilead synthesis was not changed. However, significant improvements in each step led to a doubled overall yield, a 30% reduction in the number of unit operations, and an excellent quality (≥99%) of the resulting epoxide. A highly regioselective method for the dehydration of a quinic acid to a shikimic acid derivative and for the reduction of a cyclic ketal was found. Alternatively, the title compound was synthesized in six chemical steps and 63−65% yield from commercially available (−)-shikimic acid. Compared to the optimized quinic acid route, the production time was reduced by about 50%. The quality of epoxide produced from either natural product was equivalent. Therefore (−)-shikimic acid is the preferred raw material. The absolute configuration of the epoxide was determined by X-ray single crystal structure analysis and it was demonstrated that the epoxide was stereoisomerically pure.
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