| 摘要 |
<p>An optically active tropinone monocarboxylic acid ester derivative, which is useful as an intermediate in synthesizing an optically active tropane derivative, is reacted with succinedialdehyde, an organic amine and acetone dicarboxylic acid ester to thereby give a tropinone dicarboxylic acid ester derivative. Then, the obtained product is subjected to enzymatic asymmetric dealkoxycarbonylation followed by reduction and dehydration to thereby give anhydroecgonine methyl ester. The thus obtained anhydroecgonine methyl ester shows the same optical rotation as anhydroecgonine methyl ester obtained from natural cocaine, which indicates that the former product has the same absolute configuration as the latter. In the asymmetric dealkoxycarbonylation, the optically active tropinone monocarboxylic acid ester derivative is obtained at a yield of 30 to 50 mol% and shows an optical purity of 70 to 97 %ee. By further reducing and dehydrating the optically active tropinone monocarboxylic acid ester derivative, a crystalline optically active anhydroecgonine carboxylic acid derivative can be obtained. Thus, it is found out that the optical purity can be easily elevated by recrystallization.</p> |
