以化學法探討天然物Antrocin的外消旋中間物之光學分割

在之前Antrocin的全合成文獻中所得到的最終產物都是外消旋混合物，因此本論文試著利用光學分割得到單一鏡像的Antrocin，我們以2,2-二甲基環己酮為起始物合成了具有三環主架構且帶有醇基的外消旋中間物105和129。接著將這些外消旋中間物與六種掌性試劑進行酯化反應。雖然這些外消旋中間物成功轉變為非鏡像異構物，可是我們依然無法利用管柱層析的方式分離這些非鏡像構物。此外我們還以105為起始物藉由硼氫化-氧化反應合成了外消旋中間物139和142。可是我們無法由外消旋中間物139和142合成出非鏡像異構物。這些非鏡像異構物皆無法成功分離。

關鍵字

安卓幸；光學分割；外消旋

並列摘要

In previous reports, the total synthesis of antrocin has been developed but it was obtained as a racemic mixture. Therefore, we attempted to obtain enantiomerically pure antrocin by optical resolution of its intermediates. For the optical resolution, we have synthesized two racemic intermediate 105and 129 containing tricyclic core structure and hydroxyl group starting from 2,2-methylcyclohexanone. The racemic intermediates then reacted with six chiral reagents by esterification. However, two racemic intermediates 105 and 129 were converted to diastereomers and we could not separate diastereomers by column chromatography. Furthermore, we have synthesized another racemic intermediates 139 and 142 from 105 by hydroboration-oxidation reaction. Then, we could not obtain diastereomers from racemic intermediates 139 and 142. These diastereomers could not be separated.